Ethyl 4-chloroacetoacetate → 7-(chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1896332Notes

Reaction equation

HRID 1896332 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.[Cl:8][CH2:9][C:10](=O)[CH2:11][C:12](OCC)=[O:13]>>[Cl:8][CH2:9][C:10]1[N:1]=[C:2]2[S:3][CH:4]=[C:5]([CH3:7])[N:6]2[C:12](=[O:13])[CH:11]=1

Participants

3

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 741432-Amino-4-methylthiazole

Product 1

HCID 43541347-(chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 85.3%

Procedure

This compound was synthesized from 2-amino-4-methyl thiazole (5.0 g, 43.710 mmol) and ethyl chloroacetoacetate (9.893 g, 59.561 mmol) in polyphosphoric acid (40.0 g) according to the procedure described in Step 1, Intermediate 2 to afford 8.0 g of the desired compound as a black solid; 1H NMR (300 MHz, DMSO-d6) δ 2.67 (s, 3H), 4.53 (s, 2H), 6.27 (s, 1H), 7.05 (s, 1H); ESI-MS (m/z) 215.39 (M+H)+.

Sources & evidence

ORD record
ord-7e98f51fdf034bcdb39d63ad2acf32ac
Source dataset
uspto-grants-2013_08
Patent number
US08518955B2

Reaction notes

Loading…