Formamide → HCID 178508717, compound

HRID 897448Notes

Reaction equation

HRID 897448 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)[NH:4][N:3]=1.O.[CH:23]([NH2:25])=O>>[NH2:8][C:7]1[N:25]=[CH:23][N:1]=[C:2]2[NH:3][N:4]=[C:5]([C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:11][CH:10]=3)[C:6]=12

Participants

4

Reactant 3

HCID 713FormamideHCID 962WaterHCID 223467843-amino-5-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 178508717HCID 178508717, compoundYield 80%

Conditions

Temperature
180 °C

Procedure

3-Amino-4-Cyano-5-(4-phenoxyphenyl)pyrazole (Intermediate AB) (29.5 g) was suspended in 300 mL formamide and heated under nitrogen at 180° C. for 4 hours, cooled to 3° C., 300 mL water added and the solid collected, washed well with water then methanol and dried in air giving 24.6 g pure product (80%) of 4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d] pyrimidine m.p. 267-269° C. as pale brown-grey solid. Calculated for C17H13N5O C, 67.3; H, 4.3; N, 23.1; Found C, 67.0; H, 4.4; N, 23.1

Workup

  1. temperaturecooled to 3° C.
  2. customthe solid collected
  3. washwashed well with water
  4. dry with materialmethanol and dried in air

Sources & evidence

ORD record
ord-8dc5f9dcb0e74967aadf3683c04308e3
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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