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

HRID 1602230Notes

Reaction equation

HRID 1602230 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[NH:4][N:3]=1.[CH3:19][NH:20][C:21]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O)=[O:22].C(O)(=O)C.[BH3-]C#N.[Na+]>CO.CN1C(=O)N(C)CC1>[Cl:18][C:14]1[CH:13]=[C:12]([NH:11][C:9]2[N:8]=[CH:7][N:6]=[C:5]3[NH:4][N:3]=[C:2]([NH:1][CH2:26][C:25]4[CH:28]=[CH:29][CH:30]=[C:23]([C:21]([NH:20][CH3:19])=[O:22])[CH:24]=4)[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 220514333-formyl-N-methylbenzamideHCID 178509242HCID 178509242, compound

Product 1

HCID 196105834-(3-chloro-phenylamino)-3-[3-(methylaminocarbonyl)-benzylamino]-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 2

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

Procedure

A solution of 261 mg (1.0 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 15.1) and 245 mg (1.5 mmol) of 3-(methylamino-carbonyl)-benzaldehyde in 26 ml of methanol, 26 ml of DMEU and 180 mg (3.0 mmol) of acetic acid is stirred for 1 hour at RT. Then 440 mg (7.0 mmol) of NaCNBH3 are added and the reaction mixture is stirred for 9 days at RT. The methanol is evaporated off from the reaction solution using a rotary evaporator, the residue is poured into 0.6 liter of water and stirring is carried out overnight. The product precipitates. Filtering with suction, washing with water, stirring twice in 10 ml of boiling ethanol, cooling and filtering yield 4-(3-chloro-phenylamino)-3-[3-(methylaminocarbonyl)-benzylamino]-1H-pyrazolo[3,4-d]pyrimidine; m.p. 252-254° C.; HPLC: TRet (Grad5-40)=16.9; FAB-MS: (M+H)+ =408.

Workup

  1. customThe methanol is evaporated off from the reaction solution
  2. customa rotary evaporator
  3. additionthe residue is poured into 0.6 liter of water
  4. stirringstirring
  5. waitis carried out overnight
  6. customThe product precipitates
  7. filtrationFiltering with suction
  8. washwashing with water
  9. stirringstirring twice in 10 ml of boiling ethanol
  10. temperaturecooling
  11. filtrationfiltering

Sources & evidence

ORD record
ord-42586daa614943f0850bdb2f30f7c12a
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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