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

HRID 1602232노트

반응식

HRID 1602232 반응식
[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

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 66611,3-Dimethyl-2-imidazolidinone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9cea1b37282344b8b7cb280238524367
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05981533

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