N-Iodosuccinimide → 6-Iodo-7-[(E)-2-(2-isobutoxy-3-methoxyphenyl)vinyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1896326Notes

Reaction equation

HRID 1896326 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1/[CH:14]=[CH:15]/[C:16]1[N:17]=[C:18]2[S:25][CH:24]=[CH:23][N:19]2[C:20](=[O:22])[CH:21]=1)[CH:2]([CH3:4])[CH3:3].[I:26]N1C(=O)CCC1=O>C(#N)C>[I:26][C:21]1[C:20](=[O:22])[N:19]2[CH:23]=[CH:24][S:25][C:18]2=[N:17][C:16]=1/[CH:15]=[CH:14]/[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:6]=1[O:5][CH2:1][CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 667527727-[(E)-2-(2-Isobutoxy-3-methoxyphenyl)vinyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 667529766-Iodo-7-[(E)-2-(2-isobutoxy-3-methoxyphenyl)vinyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of Step 1 intermediate (600 mg, 1.683 mmol) was treated with N-iodosuccinimide (416 g, 1.851 mmol) in acetonitrile (10 ml) according to the procedure described in Step 4 of Intermediate 2 to afford 600 mg of the desired compound as a yellow solid; 1H NMR (300 MHz, DMSO-d6) 1.05 (d, J=6.9 Hz, 6H), 2.04-2.08 (m, 1H), 3.71 (d, J=6.3 Hz, 2H), 3.81 (s, 3H), 7.10-7.12 (m, 2H), 7.27-7.30 (m, 1H), 7.48-7.53 (m, 2H), 7.96 (d, J=4.8 Hz, 1H), 8.17 (d, J=15.6 Hz, 1H); ESI-MS (m/z) 483.16 (M+H)+.

Sources & evidence

ORD record
ord-819d7519c772499d97d461e2739ec030
Source dataset
uspto-grants-2013_08
Patent number
US08518955B2

Reaction notes

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