Acetic Acid → 4-(3-chloro-phenylamino)-3-[(3-methoxy-4-hydroxy-benzyl)-amino]-1H-pyrazolo[3,4-d]pyrimidine

HRID 1602232Notes

Reaction equation

HRID 1602232 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].N#N.[NH2:14][C:15]1[C:23]2[C:18](=[N:19][CH:20]=[N:21][C:22]=2[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)[NH:17][N:16]=1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO.CN1C(=O)N(C)CC1.O>[Cl:31][C:27]1[CH:26]=[C:25]([NH:24][C:22]2[N:21]=[CH:20][N:19]=[C:18]3[NH:17][N:16]=[C:15]([NH:14][CH2:6][C:5]4[CH:8]=[CH:9][C:2]([OH:1])=[C:3]([O:10][CH3:11])[CH:4]=4)[C:23]=23)[CH:30]=[CH:29][CH:28]=1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 947NitrogenHCID 1183VanillinHCID 5003444Sodium cyanoborohydrideHCID 178509242HCID 178509242, compound

Product 1

HCID 196106164-(3-chloro-phenylamino)-3-[(3-methoxy-4-hydroxy-benzyl)-amino]-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

228 mg (1.50 mmol) of 4-hydroxy-3-methoxy-benzaldehyde are added (N2 atmosphere) to a solution of 261 mg (1.00 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine in 26 ml of methanol, 26 ml of DMEU and 120 mg (2.0 mmol) of acetic acid. After 1 hour, 440 mg (7.0 mmol) of NaCNBH3 are added to the clear solution and stirring is then carried out at RT for 7 days. The reaction solution is poured into 0.8 liter of water and stirred overnight to complete the reaction, during which time the product precipitates. Filtering with suction, washing with water, stirring in hot ethyl acetate, cooling and filtering yield 4-(3-chloro-phenylamino)-3-[(3-methoxy-4-hydroxy-benzyl)-amino]-1H-pyrazolo[3,4-d]pyrimidine; m.p. 223-225° C.; HPLC: TRet (Grad5-40)=19.8; FAB-MS: (M+H)+ =397.

Workup

  1. waitis then carried out at RT for 7 days
  2. stirringstirred overnight
  3. customthe reaction
  4. customduring which time the product precipitates
  5. filtrationFiltering with suction
  6. washwashing with water
  7. stirringstirring in hot ethyl acetate
  8. temperaturecooling
  9. filtrationfiltering

Sources & evidence

ORD record
ord-9cea1b37282344b8b7cb280238524367
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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