Ethyl 4-chloroacetoacetate → 2-chloro-7-chloromethyl-5H-thiazolo[3,2-a]pyrimidine-5-one

HRID 1642402Notes

Reaction equation

HRID 1642402 reaction equation
C1(COC2C(OC)=CC=CC=2/C=C/C2N=C3SC=CN3C(=O)C=2I)CC1.Cl.[Cl:28][C:29]1[S:33][C:32]([NH2:34])=[N:31][CH:30]=1.[Cl:35][CH2:36][C:37](=O)[CH2:38][C:39](OCC)=[O:40]>>[Cl:28][C:29]1[S:33][C:32]2=[N:34][C:37]([CH2:36][Cl:35])=[CH:38][C:39](=[O:40])[N:31]2[CH:30]=1

Participants

4

Reactant 3

HCID 69484Ethyl 4-chloroacetoacetateHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 66753592HCID 66753592, compound

Product 1

HCID 131058502-chloro-7-chloromethyl-5H-thiazolo[3,2-a]pyrimidine-5-oneYield 124.1%

Procedure

Step 1: This compound was prepared according to the procedure outlined in Intermediate 2, Step 1 using 5-chloro-1,3-thiazol-2-amine hydrochloride (3.01 g, 17.482 mmol) polyphosphoric acid (81.0 g) and ethyl chloroacetoacetate (4.03 g, 24.475 mmol) to afford 5.1 g of the desired compound as a brown solid: 1H NMR (300 MHz, DMSO-d6) δ 4.55 (s, 2H), 6.45 (s, 1H), 8.31 (s, 1H); ESI-MS (m/z) 235.57 (M+H)+.

Workup

  1. customStep 1: This compound was prepared

Sources & evidence

ORD record
ord-35dee39824ed4e0aaacfe955fbbb939c
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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