Tert-Butylamine → 6-(N-tert.-Butyl-carbamoyl)-4-(3-chloro-anilino)-7H-pyrrolo[2,3-d]pyrimidine

HRID 369872노트

반응식

HRID 369872 반응식
[C:1]([C:4]1[NH:20][C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:6]=2[CH:5]=1)([OH:3])=O.[C:21]([NH2:25])([CH3:24])([CH3:23])[CH3:22].C(P(=O)(OCC)OCC)#N>CN(C=O)C>[C:21]([NH:25][C:1]([C:4]1[NH:20][C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:6]=2[CH:5]=1)=[O:3])([CH3:24])([CH3:23])[CH3:22]

참가 물질

5

반응물 3

HCID 6385Tert-ButylamineHCID 76257Diethyl cyanophosphonateHCID 212626746-carboxy-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

생성물 1

HCID 232827596-(N-tert.-Butyl-carbamoyl)-4-(3-chloro-anilino)-7H-pyrrolo[2,3-d]pyrimidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 144 mg (0.50 mmol) of 6-carboxy-4-(3-chloro-anilino)-7H-pyrrolo[2,3-d]pyrimidine (cf. Example 42) and 116 μl (1.1 mmol) of tert.-butylamine in 5 ml of DMF are added 114 μl (0.75 mmol) of diethyl cyanophosphonate (Aldrich; Milwaukee/USA). After 4 h, the reaction mixture is poured onto ice water, stirred for 30 min and finally filtered. The residue is redissolved in isopropanol, treated with charcoal and filtered. Concentration in vacuo and washing with dichloromethane/diethyl ether yields the title compound; HPLC: tRet (Grad20)=11.4; FAB-MS: (M+H)+ =344.

후처리

  1. additionthe reaction mixture is poured onto ice water
  2. filtrationfinally filtered
  3. dissolutionThe residue is redissolved in isopropanol
  4. additiontreated with charcoal
  5. filtrationfiltered
  6. concentrationConcentration in vacuo
  7. washwashing with dichloromethane/diethyl ether

출처 및 근거

ORD 기록
ord-015f9b952a0447c4ac4918724c83e99a
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140332

반응 노트

불러오는 중…