Acetic Acid → 4-(3-chloro-phenylamino)-3-(3,5-dimethoxybenzylamino)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1602231Notes

Reaction equation

HRID 1602231 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=O.[NH2:13][C:14]1[C:22]2[C:17](=[N:18][CH:19]=[N:20][C:21]=2[NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[NH:16][N:15]=1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO.O>[Cl:30][C:26]1[CH:25]=[C:24]([NH:23][C:21]2[N:20]=[CH:19][N:18]=[C:17]3[NH:16][N:15]=[C:14]([NH:13][CH2:6][C:5]4[CH:4]=[C:3]([O:2][CH3:1])[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=4)[C:22]=23)[CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 817473,5-DimethoxybenzaldehydeHCID 5003444Sodium cyanoborohydride2×HCID 178509242HCID 178509242, compound2×

Product 1

HCID 196106434-(3-chloro-phenylamino)-3-(3,5-dimethoxybenzylamino)-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

99.7 mg (0.60 mmol) of 3,5-dimethoxy-benzaldehyde are added to a solution of 130 mg (0.50 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine in 26 ml of methanol and 120 mg (2.0 mmol) of acetic acid. As the reaction mixture is stirred, a solid precipitates which can be dissolved again by the addition of 52 ml of DMEU. 220 mg (3.5 mmol) of NaCNBH3 are added thereto and stirring is then continued for 5 hours at RT. Since not all of the 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine has been reacted (HPLC), 220 mg of NaCNBH3 are added twice more and stirring is continued for 5 hours each time. The reaction solution is then poured into 1 liter of water, stirred vigorously for 1 hour and filtered. Crystallization of the filtration residue from acetone yields 4-(3-chloro-phenylamino)-3-(3,5-dimethoxybenzylamino)-1H-pyrazolo[3,4-d]pyrimidine; m.p. 208-209° C.; HPLC: TRet (Grad20-100)=11.7; FAB-MS: (M+H)+ =411.

Workup

  1. customa solid precipitates which
  2. dissolutioncan be dissolved again by the addition of 52 ml of DMEU
  3. stirringstirring
  4. additionare added twice more
  5. stirringstirring
  6. waitis continued for 5 hours
  7. stirringstirred vigorously for 1 hour
  8. filtrationfiltered
  9. customCrystallization of the filtration residue from acetone

Sources & evidence

ORD record
ord-41b7a7ad20464249ae25ee88792079d5
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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