Methanol → HCID 178482795, compound

HRID 1068946Notes

Reaction equation

HRID 1068946 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:18]3[C:13](=[N:14][CH:15]=[N:16][C:17]=3[NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[NH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.C(O[CH:30](OCC)[N:31](C)[CH3:32])C.[CH3:37]O>>[Cl:26][C:22]1[CH:21]=[C:20]([NH:19][C:17]2[N:16]=[CH:15][N:14]=[C:13]3[NH:12][N:11]=[C:10]([NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([CH:2]([N:31]([CH3:32])[CH3:30])[N:1]=[CH2:37])[CH:4]=4)[C:18]=23)[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 70913Dimethylformamide diethylacetalHCID 178509838HCID 178509838, compound

Product 1

HCID 178482795HCID 178482795, compound

Conditions

Temperature
30 °C

Procedure

A mixture of 500 mg (1.34 mmol) of 3-(3aminomethyl-phenylamino)4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (water content: 1.79%), 402 mg (2.73 mmol) of N,N-dimethylformamide diethyl acetal and 5 ml of methanol is stirred at 30° C. for 2 hours and then concentrated by evaporation in vacuo. Crystallisation of the residue from ethyl acetate, filtration and washing the filter residue with ethyl acetate yield 4-(3-chloro-phenylamino)-3-[3-(dimethylamino-methyleneamino-methyl)-phenylamino]-1H-pyrazolo[3,4-d]pyrimidine having a water content of 1.68%; m.p. 175-177° C.; ESI-MS: (M+H)+=421.

Workup

  1. concentrationconcentrated by evaporation in vacuo
  2. customCrystallisation of the residue
  3. filtrationfrom ethyl acetate, filtration
  4. washwashing the filter residue with ethyl acetate

Sources & evidence

ORD record
ord-961ad0fe05634e198d66903dfa1cbf2a
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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