2-Aminothiazole → 7-Methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-one

HRID 1642376Notes

Reaction equation

HRID 1642376 reaction equation
NC1SC=CN=1.C(OCC)(=O)CC(C)=O.FC1C=C([C:24]2[C:29](=[O:30])[N:28]3[CH:31]=[CH:32][S:33][C:27]3=[N:26][C:25]=2[CH3:34])C=C(F)C=1>C(O)(=O)C>[CH3:34][C:25]1[N:26]=[C:27]2[S:33][CH:32]=[CH:31][N:28]2[C:29](=[O:30])[CH:24]=1

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 8868Ethyl AcetoacetateHCID 667534716-(3,5-Difluorophenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 5970657-Methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-aminothiazole (50 g, 499.301 mmol), ethyl acetoacetate (96 ml, 748.885 mmol) and acetic acid (400 ml) was reacted together according to the procedure described in Intermediate 3, Step 1 to afford a crude product which was purified by silica gel column chromatography using 1% methanol in chloroform to give 40 g of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 2.38 (s, 3H), 6.15 (s, 1H), 6.95 (d, J=4.8 Hz, 1H), 7.94 (d, J=4.8 Hz, 1H).

Workup

  1. customto afford a crude product which
  2. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b7f64078e95c4237918e47578244a91b
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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