Iodine → 6-Iodo-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1642377Notes

Reaction equation

HRID 1642377 reaction equation
II.ClC1C=CC(/C=[CH:11]/[C:12]2[N:13]=[C:14]3[S:22][CH:21]=[CH:20][N:15]3[C:16](=[O:19])[C:17]=2[I:18])=CC=1>C(#N)C>[I:18][C:17]1[C:16](=[O:19])[N:15]2[CH:20]=[CH:21][S:22][C:14]2=[N:13][C:12]=1[CH3:11]

Participants

4

Reactant 2

HCID 807IodineHCID 66753972HCID 66753972, compound

Product 1

HCID 667535716-Iodo-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of the Step 1 intermediate (20 g, 120.463 mmol) in acetonitrile (200 ml) was reacted with ceric ammonium nitrate (33 g, 60.233 mmol) followed by iodine (18 g, 72.281 mmol) according to the procedure described in Intermediate 1, Step 3 to give 35 g of the product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 2.56 (s, 3H), 7.52 (d, J=5.1 Hz, 1H), 7.97 (d, J=4.8 Hz, 1H); ESI-MS (m/z) 291.29 (M−H)−.

Sources & evidence

ORD record
ord-f7b78c2b2502407f81e80b5b80372fe7
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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