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

HRID 1896325Notes

Reaction equation

HRID 1896325 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7](OCC)(=[O:12])[CH2:8][C:9]([CH3:11])=O>C(O)(=O)C>[CH3:11][C:9]1[N:1]=[C:2]2[S:3][CH:4]=[CH:5][N:6]2[C:7](=[O:12])[CH:8]=1

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 8868Ethyl Acetoacetate

Product 1

HCID 5970657-Methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-oneYield 48.2%

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-afabc9c2256945ddbad32f6c5b02c61f
Source dataset
uspto-grants-2013_08
Patent number
US08518955B2

Reaction notes

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