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Pivalaldehyde → 4-(3-chloro-phenylamino)-3-(2,2-dimethylpropyl-amino)-1H-pyrazolo[3,4-d]pyrmidine

HRID 1068933
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인쇄 미리보기

반응식

HRID 1068933 반응식
[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][C:20]([CH:23]=O)([CH3:22])[CH3:21].[BH3-]C#N.[Na+].N1C2C=NC=NC=2C=N1>CN1C(=O)N(C)CC1.CO.CCCCCC.C(O)(=O)C>[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][CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]=23)[CH:17]=[CH:16][CH:15]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 12417Pivalaldehyde2회HCID 5003444Sodium cyanoborohydride2회HCID 210839761H-pyrazolo(4,3-d)pyrimidineHCID 178509242HCID 178509242, 화합물

생성물 1

HCID 696959324-(3-chloro-phenylamino)-3-(2,2-dimethylpropyl-amino)-1H-pyrazolo[3,4-d]pyrmidine

시약·촉매·용매 3

HCID 176
Acetic Acid
용매
2회
HCID 8058Hexane용매
HCID 131722711DMEU methanol용매

실험 절차

Analogously to Example 34, 261 mg (1.00 mmol) of 3-amino-4-(3-chlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6), 129 mg (1.5 mmol) of pivaldehyde and 180 mg of acetic acid are stirred in 39 ml of DMEU/methanol (1:2) and then reacted with 440 mg (7 mmol) of NaCNBH3. Since, according to HPLC, the reaction is incomplete, 129 mg of pivaldehyde, 180 mg of acetic acid and 440 mg of NaCNBH3 are added a number of times until HPLC indicates that all the pyrazolo-pyrimidine has reacted. Between the individual additions, the reaction mixture is stirred at boiling temperature for 20 hours each time. Analogous working-up and stirring in hexane yield 4-(3-chloro-phenylamino)-3-(2,2-dimethylpropyl-amino)-1H-pyrazolo[3,4-d]pyrmidine; m.p. 229-231° C.; HPLC: tRet(grad20-100/20)=11.6; FAB-MS: (M+H)+=331.

후처리

  1. customhas reacted
  2. customfor 20 hours

출처 및 근거

ORD 기록
ord-1375eb25c0ac451791375db652d11df5
출처 데이터셋
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06251911B1

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