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

HRID 1642382Notes

Reaction equation

HRID 1642382 reaction equation
C(OC1C(OC)=CC=CC=1/C=C/C1N=C2SC=CN2C(=O)C=1)C(C)C.IN1C(=O)CCC1=O.[CH:34]1([CH2:37][O:38][C:39]2[C:44]([O:45][CH3:46])=[CH:43][CH:42]=[CH:41][C:40]=2/[CH:47]=[CH:48]/[C:49]2[N:50]=[C:51]3[S:59][CH:58]=[CH:57][N:52]3[C:53](=[O:56])[C:54]=2[I:55])[CH2:36][CH2:35]1>C(#N)C>[I:55][C:54]1[C:53](=[O:56])[N:52]2[CH:57]=[CH:58][S:59][C:51]2=[N:50][C:49]=1/[CH:48]=[CH:47]/[C:40]1[CH:41]=[CH:42][CH:43]=[C:44]([O:45][CH3:46])[C:39]=1[O:38][CH2:37][CH:34]([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 667527727-[(E)-2-(2-Isobutoxy-3-methoxyphenyl)vinyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneHCID 66753592HCID 66753592, compound

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-32576800e0b84a65b20b191b1f75c346
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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