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

HRID 912674

Reaction equation

HRID 912674 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C(OC(C)(C)C)=O)[CH:6]=[C:5]2[CH2:18][N:19]1[C:27]2[N:26]=[CH:25][NH:24][C:23]=2[C:22](=[O:28])[NH:21][C:20]1=[S:29].C1C(I)=C(OC2C=C(I)C(O)=C(I)C=2)C(I)=CC=1C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:18][N:19]1[C:27]2[N:26]=[CH:25][NH:24][C:23]=2[C:22](=[O:28])[NH:21][C:20]1=[S:29]

Participants

4

Reactant 2

HCID 64513523,3',5,5'-Tetraiodothyroformic acidHCID 86631122HCID 86631122, compound

Product 1

HCID 248555003-[(5-chloro-1H-indol-3-yl)methyl]-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-oneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 5-chloro-3-[(6-oxo-2-thioxo-1,2,6,7-tetrahydro-3H-purin-3-yl)methyl]-1H-indole-1-carboxylate (0.043 g, 0.10 mmol, obtained from Example 10(c)) in CH2Cl2:TFA 4:1 (2 mL) was stirred for 3.5 h and then evaporated. Purification of the crude product by preparative HPLC gave the title compound (0.022 g, 68%) as a solid.

Workup

  1. customevaporated
  2. customPurification of the crude product by preparative HPLC

Sources & evidence

ORD record
ord-24220a6edfb24459b66750bd182258b7
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Linked notes

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