3,3',5,5'-Tetraiodothyroformic acid → 3-[(4-fluoro-1H-indol-3-yl)methyl]-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one

HRID 912677

Reaction equation

HRID 912677 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:18][N:19]1[C:27]3[N:26]=[CH:25][NH:24][C:23]=3[C:22](=[O:28])[NH:21][C:20]1=[S:29])=[CH:5][N:6]2C(OC(C)(C)C)=O.C1C(I)=C(OC2C=C(I)C(O)=C(I)C=2)C(I)=CC=1C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:18][N:19]1[C:27]3[N:26]=[CH:25][NH:24][C:23]=3[C:22](=[O:28])[NH:21][C:20]1=[S:29])=[CH:5][NH:6]2

Participants

4

Reactant 2

HCID 64513523,3',5,5'-Tetraiodothyroformic acidHCID 86631124HCID 86631124, compound

Product 1

HCID 248555013-[(4-fluoro-1H-indol-3-yl)methyl]-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-oneYield 42.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-fluoro-3-[(6-oxo-2-thioxo-1,2,6,7-tetrahydro-3H-purin-3-yl)methyl]-1H-indole-1-carboxylate (0.089 g, 0.21 mmol, obtained from Example 11(c)) in CH2Cl2:TFA 4:1 (1 mL) was stirred for 1 h 40 minutes and then evaporated. The crude product was purified by preparative HPLC, giving the title compound (0.028 g, 42%) as a solid.

Workup

  1. customevaporated
  2. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-5dfd4f60facf438d8f3a6c26c5f9565f
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Linked notes

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