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

HRID 1642393Notes

Reaction equation

HRID 1642393 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][N:6]=1.[Cl:8][CH2:9][C:10](=O)[CH2:11][C:12](OCC)=[O:13].C1(COC2C(OC)=CC=CC=2/C=C/C2N=C3SC=CN3C(=O)C=2I)CC1>>[Cl:8][CH2:9][C:10]1[N:1]=[C:2]2[S:3][C:4]([CH3:7])=[CH:5][N:6]2[C:12](=[O:13])[CH:11]=1

Participants

4

Reactant 3

HCID 69484Ethyl 4-chloroacetoacetateHCID 3517702-Amino-5-methylthiazoleHCID 66753592HCID 66753592, compound

Product 1

HCID 176047167-(chloromethyl)-2-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 63.9%

Procedure

This compound was synthesized from 2-amino-5-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 6.0 g of the desired compound as a black solid; 1H NMR (300 MHz, DMSO-d6) δ 2.43 (s, 3H), 4.58 (s, 2H), 6.39 (s, 1H), 7.87 (s, 1H); ESI-MS (m/z) 215.37 (M+H)+.

Sources & evidence

ORD record
ord-e3de6f6f715c42d490a90dd091f0c515
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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