Selective alkylation of pyrimidyl dianions III: No-carrier-added synthesis of [11C-methyl]-thymidine

Mian M. Alauddin; Hayden T. Ravert; John L. Musachio; William B. Mathews; Robert F. Dannals; Peter S. Conti

doi:10.1016/0969-8051(95)00027-U

Selective alkylation of pyrimidyl dianions III: No-carrier-added synthesis of [¹¹C-methyl]-thymidine

Mian M. Alauddin, Hayden T. Ravert, John L. Musachio, William B. Mathews, Robert F. Dannals, Peter S. Conti

School of Medicine

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

A no-carrier-added, high specific activity synthesis of [¹¹C-methyl]-thymidine is reported. Reaction of 3′, 5′-O-bis-(tetrahydropyranyl)-5-bromo-2′-deoxyuridine with n-butyllithium produced a dianion which was alkylated with [¹¹C]-methyl iodide, and on subsequent hydrolysis, yielded [¹¹C-methyl]-thymidine. The labeled compound was isolated from the by-product 2′-deoxyuridine by HPLC on a reverse phase C₁₈ semipreparative column with mean radiochemical yield of 18.8% (decay corrected) in 30-35 min and radiochemical purity >99%. This no-carrier-added synthesis can be used to produce [¹¹C-methyl]-thymidine with mean specific activity over 1000 mCi/μmol for positron emission tomography (PET) studies.

Original language	English (US)
Pages (from-to)	791-794
Number of pages	4
Journal	Nuclear Medicine and Biology
Volume	22
Issue number	6
DOIs	https://doi.org/10.1016/0969-8051(95)00027-U
State	Published - Aug 1995

ASJC Scopus subject areas

Molecular Medicine
Radiology Nuclear Medicine and imaging
Cancer Research

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@article{9a75c6a11e55477dbd7bb2d0bda4d6ad,

title = "Selective alkylation of pyrimidyl dianions III: No-carrier-added synthesis of [11C-methyl]-thymidine",

abstract = "A no-carrier-added, high specific activity synthesis of [11C-methyl]-thymidine is reported. Reaction of 3′, 5′-O-bis-(tetrahydropyranyl)-5-bromo-2′-deoxyuridine with n-butyllithium produced a dianion which was alkylated with [11C]-methyl iodide, and on subsequent hydrolysis, yielded [11C-methyl]-thymidine. The labeled compound was isolated from the by-product 2′-deoxyuridine by HPLC on a reverse phase C18 semipreparative column with mean radiochemical yield of 18.8% (decay corrected) in 30-35 min and radiochemical purity >99%. This no-carrier-added synthesis can be used to produce [11C-methyl]-thymidine with mean specific activity over 1000 mCi/μmol for positron emission tomography (PET) studies.",

author = "Alauddin, {Mian M.} and Ravert, {Hayden T.} and Musachio, {John L.} and Mathews, {William B.} and Dannals, {Robert F.} and Conti, {Peter S.}",

note = "Funding Information: Acknowledgemenr-Thea uthorsw ish to thank Mr. Robert Smootf or his assistanceT.h is work was supportedin partb y NIH grant CA 37870-08U, SPHS grant NS15080a nd NC1 trainingg rantC A 09199.",

year = "1995",

month = aug,

doi = "10.1016/0969-8051(95)00027-U",

language = "English (US)",

volume = "22",

pages = "791--794",

journal = "Nuclear Medicine and Biology",

issn = "0969-8051",

publisher = "Elsevier Inc.",

number = "6",

}

TY - JOUR

T1 - Selective alkylation of pyrimidyl dianions III

T2 - No-carrier-added synthesis of [11C-methyl]-thymidine

AU - Alauddin, Mian M.

AU - Ravert, Hayden T.

AU - Musachio, John L.

AU - Mathews, William B.

AU - Dannals, Robert F.

AU - Conti, Peter S.

N1 - Funding Information: Acknowledgemenr-Thea uthorsw ish to thank Mr. Robert Smootf or his assistanceT.h is work was supportedin partb y NIH grant CA 37870-08U, SPHS grant NS15080a nd NC1 trainingg rantC A 09199.

PY - 1995/8

Y1 - 1995/8

N2 - A no-carrier-added, high specific activity synthesis of [11C-methyl]-thymidine is reported. Reaction of 3′, 5′-O-bis-(tetrahydropyranyl)-5-bromo-2′-deoxyuridine with n-butyllithium produced a dianion which was alkylated with [11C]-methyl iodide, and on subsequent hydrolysis, yielded [11C-methyl]-thymidine. The labeled compound was isolated from the by-product 2′-deoxyuridine by HPLC on a reverse phase C18 semipreparative column with mean radiochemical yield of 18.8% (decay corrected) in 30-35 min and radiochemical purity >99%. This no-carrier-added synthesis can be used to produce [11C-methyl]-thymidine with mean specific activity over 1000 mCi/μmol for positron emission tomography (PET) studies.

AB - A no-carrier-added, high specific activity synthesis of [11C-methyl]-thymidine is reported. Reaction of 3′, 5′-O-bis-(tetrahydropyranyl)-5-bromo-2′-deoxyuridine with n-butyllithium produced a dianion which was alkylated with [11C]-methyl iodide, and on subsequent hydrolysis, yielded [11C-methyl]-thymidine. The labeled compound was isolated from the by-product 2′-deoxyuridine by HPLC on a reverse phase C18 semipreparative column with mean radiochemical yield of 18.8% (decay corrected) in 30-35 min and radiochemical purity >99%. This no-carrier-added synthesis can be used to produce [11C-methyl]-thymidine with mean specific activity over 1000 mCi/μmol for positron emission tomography (PET) studies.

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U2 - 10.1016/0969-8051(95)00027-U

DO - 10.1016/0969-8051(95)00027-U

M3 - Article

C2 - 8535340

AN - SCOPUS:0029089004

SN - 0969-8051

VL - 22

SP - 791

EP - 794

JO - Nuclear Medicine and Biology

JF - Nuclear Medicine and Biology

IS - 6

ER -

Selective alkylation of pyrimidyl dianions III: No-carrier-added synthesis of [¹¹C-methyl]-thymidine

Abstract

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