Formamide → 3-(4-Nitrophenyl)isothiazolo[5,4-d]pyrimidin-4-amine

HRID 227618Notes

Reaction equation

HRID 227618 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=O)=[CH:9][CH:8]=2)[C:3]=1[C:16]#[N:17].[OH2:18].[CH:19]([NH2:21])=O>>[N+:13]([C:10]1[CH:9]=[CH:8][C:7]([C:4]2[C:3]3[C:2](=[N:1][CH:19]=[N:21][C:16]=3[NH2:17])[S:6][N:5]=2)=[CH:12][CH:11]=1)([O-:15])=[O:18]

Participants

4

Reactant 3

HCID 713FormamideHCID 962WaterHCID 690551855-Amino-3-(4-nitrophenyl)isothiazole-4-carbonitrile

Product 1

HCID 444147423-(4-Nitrophenyl)isothiazolo[5,4-d]pyrimidin-4-amineYield 84%

Procedure

A mixture of Example 96E (200 mg) in formamide (5 mL) in a capped vial was heated to 210° C. in a Smith microwave oven at 300W for 25 minutes, poured into water, and filtered. The filter cake was dried to provide 2.02 g (84% yield) of the desired product. MS(ESI(+)) m/e 274 (M+H)+.

Workup

  1. filtrationfiltered
  2. customThe filter cake was dried

Sources & evidence

ORD record
ord-cb325f8a8a724487b8bc4591735c1aec
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

Loading…