HCID 54757213, compound → HCID 135677718, compound

HRID 1782131Notes

Reaction equation

HRID 1782131 reaction equation
[C:1]([NH:6][C:7]1[S:11][N:10]=[C:9]([CH3:12])[C:8]=1[C:13]([NH2:15])=[O:14])(=O)[CH2:2][CH2:3][CH3:4]>N>[CH3:12][C:9]1[C:8]2[C:13](=[O:14])[NH:15][C:1]([CH2:2][CH2:3][CH3:4])=[N:6][C:7]=2[S:11][N:10]=1

Participants

3

Reactant 1

HCID 54757213HCID 54757213, compound

Product 1

HCID 135677718HCID 135677718, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
140 °C

Procedure

5-Butyrylamino-3-methyl-isothiazole-4-carboxylic acid amide (method 6) (1.9 g, 8.3 mmol) was suspended in 75 mL of 30% NH3 and then was heated to 140° C. for 4 h in a pressure reactor. The mixture was cooled and neutralized to pH 8. The precipitated 3-methyl-6-propyl-5H-isothiazolo[5,4-d]pyrimidin-4-one was filtered off, washed with water (100 mL) and dried in vacuum oven at 40° C. overnight to get 800 mg (34%) of pure product. 1H NMR (300 MHz) δ 1.03 (t, 3H), 1.74 (m, 2H), 2.67 (t, 3H), 2.78 (s, 3H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe precipitated 3-methyl-6-propyl-5H-isothiazolo[5,4-d]pyrimidin-4-one was filtered off
  3. washwashed with water (100 mL)
  4. customdried in vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-fe28396beac44d89a69e369124bb1b5a
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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