Acetic Anhydride → 3-(4-acetyl-piperazin-1-yl)-4-(3-chlorophenylamino)-1H-pyrazolo(3,4-d]pyrimidine

HRID 1068895Notes

Reaction equation

HRID 1068895 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[CH:15][N:14]=[C:13]3[NH:17][N:18]=[C:19]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[C:12]=23)[CH:7]=[CH:8][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[C:32](OC(=O)C)(=[O:34])[CH3:33]>O.O1CCOCC1>[C:32]([N:23]1[CH2:24][CH2:25][N:20]([C:19]2[C:12]3[C:13](=[N:14][CH:15]=[N:16][C:11]=3[NH:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=3)[NH:17][N:18]=2)[CH2:21][CH2:22]1)(=[O:34])[CH3:33]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 211906574-(3-chlorophenylamino)-3-(piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine dihydrochloride

Product 1

HCID 211906143-(4-acetyl-piperazin-1-yl)-4-(3-chlorophenylamino)-1H-pyrazolo(3,4-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Analogously to Example 26, 100 mg (0.248 mmol) of 4-(3-chlorophenylamino)-3-(piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine dihydrochloride and 103 mg (0.74 mmol) of potassium carbonate in 10 ml of water are reacted with 38 mg (0.37 mmol) of acetic anhydride in 10 ml of dioxane to form 3-(4-acetyl-piperazin-1-yl)-4-(3-chlorophenylamino)-1H-pyrazolo(3,4-d]pyrimidine; HPLC: tRet(grad20-100/20)=10.8; FAB-MS: (M+H)+=372.

Sources & evidence

ORD record
ord-effaed7608984701b4800ccc1e7cd7b5
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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