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

HRID 1602232ノート

反応式

HRID 1602232 の反応式
[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

参加物

9

反応物 5

HCID 176Acetic AcidHCID 947NitrogenHCID 1183VanillinHCID 5003444Sodium cyanoborohydrideHCID 178509242HCID 178509242、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 66611,3-Dimethyl-2-imidazolidinone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9cea1b37282344b8b7cb280238524367
出典データセット
uspto-grants-1999_11
特許番号
US05981533

反応ノート

読み込み中…