Ethyl Acetate → HCID 21190717, compound

HRID 1068912Notes

Reaction equation

HRID 1068912 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]3[NH:15][N:16]=[C:17]([N:18]=[CH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]5[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=5)=[CH:22][CH:21]=4)[C:10]=23)[CH:5]=[CH:6][CH:7]=1.C(OCC)(=O)C.[O-]S([O-])(=O)=O.[Na+].[Na+]>CN1C(=O)N(C)CC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]3[NH:15][N:16]=[C:17]([NH:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]5[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=5)=[CH:22][CH:21]=4)[C:10]=23)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 24436Sodium SulfateHCID 178478145HCID 178478145, compound

Product 1

HCID 21190717HCID 21190717, compound

Reagents, catalysts & solvents 3

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

Procedure

With ice-cooling, 10.3 ml (10.3 mmol) of DISAL-H are added to 550 mg (1.29 mmol) of 4-(3-chloro-phenylamino)-3-{[4-(pyrid-3-yl)-phenyl]-methyleneamino}-1H-pyrazolo[3,4-d]pyrimidine that have been dissolved in 25 ml of DMEU and the reaction mixture is stirred for 60 min. 15 ml of ethyl acetate are added and the mixture is stirred for 5 min and diluted with 300 ml of methanol and 1 ml of water; 20 g of Na2SO4 are added and after 15 min the mixture is filtered and the filtrate is concentrated by evaporation in a rotary evaporator. The residue is poured into 0.5 liter of water and 0.7 liter of ethyl acetate, and the aqueous phase is separated off and extracted twice more with ethyl acetate. The organic phases are washed 20 times with water (until DMEU-free) and finally with brine, dried (Na2SO4) and concentrated by evaporation. Stirring in methanol and filtration until clear and stirring in ethyl acetate and diethyl ether yield 4-(3-chloro-phenylamino)-3-[4-(pyrid-3-yl)-benzylamino]-1H-pyrazolo[3,4-d]pyrimidine; TLC: Rf=0.47 (CHCl3/methano/H2O/acetic acid=85:13:1.5:0.5); HPLC: tRet(grad20-100)=6.4; FAB-MS: (M+H)+=428.

Workup

  1. temperatureWith ice-cooling
  2. stirringthe mixture is stirred for 5 min
  3. filtrationis filtered
  4. concentrationthe filtrate is concentrated by evaporation in a rotary evaporator
  5. additionThe residue is poured into 0.5 liter of water and 0.7 liter of ethyl acetate
  6. customthe aqueous phase is separated off
  7. extractionextracted twice more with ethyl acetate
  8. washThe organic phases are washed 20 times with water (until DMEU-free)
  9. dry with materialfinally with brine, dried (Na2SO4)
  10. concentrationconcentrated by evaporation
  11. stirringStirring in methanol
  12. filtrationfiltration until clear and
  13. stirringstirring in ethyl acetate

Sources & evidence

ORD record
ord-424d3cc674a04bc7b4cadb79466a6956
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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