N-Iodosuccinimide → 7-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}-6-iodo-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1642384Notes

Reaction equation

HRID 1642384 reaction equation
[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1/[CH:13]=[CH:14]/[C:15]1[N:16]=[C:17]2[S:24][CH:23]=[CH:22][N:18]2[C:19](=[O:21])[CH:20]=1.[I:27]N1C(=O)CCC1=O.C1(COC2C(OC)=CC=CC=2/C=C/C2N=C3SC=CN3C(=O)C=2I)CC1>C(#N)C>[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1/[CH:13]=[CH:14]/[C:15]1[N:16]=[C:17]2[S:24][CH:23]=[CH:22][N:18]2[C:19](=[O:21])[C:20]=1[I:27]

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 667532687-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}-5H-[1,3]thiazolo-[3,2-a]pyrimidin-5-oneHCID 66753592HCID 66753592, compound

Product 1

HCID 667533947-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}-6-iodo-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of Step 1 intermediate (275 mg, 5.816 mmol) was treated with N-iodosuccinimide (143 g, 6.327 mmol) in acetonitrile (10 ml) according to the procedure described in Step 4 of Intermediate 2 to afford a crude product which was purified by column chromatography using 2% ethyl acetate in chloroform as eluent to afford 510 mg of the desired compound as a yellow solid; 1H NMR (300 MHz, DMSO-d6) 1.08 (s, 9H), 3.58 (m, 2H), 3.81 (m, 3H), 7.07-7.12 (m, 2H), 7.30-7.33 (m, 2H), 7.41-7.48 (m, 1H), 7.94-7.96 (m, 1H), 8.23-8.29 (m, 1H); ESI-MS (m/z) 497.21 (M+H)+.

Workup

  1. customto afford a crude product which
  2. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b65179b0cd654b7e95cbc377ac267252
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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