1,2-Dichloroethane → N-(2,4-dimethoxybenzyl)-7-((3aS,4R,6R,6aR)-6-((isopropylamino)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 511577

반응식

HRID 511577 반응식
[NH2:1][CH2:2][C@@H:3]1[C@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@H:6]2[C@H:5]([N:13]2[C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=4[O:32][CH3:33])[C:16]=3[CH:15]=[CH:14]2)[CH2:4]1.ClCCCl.[CH3:38][C:39]([CH3:41])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:33][O:32][C:25]1[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:24]=1[CH2:23][NH:22][C:21]1[C:16]2[CH:15]=[CH:14][N:13]([C@H:5]3[C@H:6]4[C@H:7]([O:8][C:9]([CH3:12])([CH3:11])[O:10]4)[C@@H:3]([CH2:2][NH:1][CH:39]([CH3:41])[CH3:38])[CH2:4]3)[C:17]=2[N:18]=[CH:19][N:20]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 677749937-((3aS,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-N-(2,4-dimethoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

생성물 1

HCID 67775374N-(2,4-dimethoxybenzyl)-7-((3aS,4R,6R,6aR)-6-((isopropylamino)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 7-((3aS,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-N-(2,4-dimethoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (7.50 g, 16.5 mmol) in 1,2-Dichloroethane (140 mL, 1800 mmol) was treated with Acetone (1.34 mL, 18.2 mmol) and Acetic acid (0.94 mL, 16 mmol) dropwise followed by Sodium triacetoxyborohydride (4.20 g, 19.8 mmol) and the mixture was stirred at RT for 4 h. HPLC analysis indicated the reaction was complete. The reaction mixture was diluted with 200 mL CH2Cl2 and washed with 150 mL sat NaHCO3. The aqueous phase was washed with 100 mL CH2Cl2 and the combined organic phase was dried over Na2SO4, filtered and concentrated to yield a an oil that produced a stiff foam when placed under high vac. The crude material (9.3 g) was carried on directly to the next step.

후처리

  1. washwashed with 150 mL
  2. washThe aqueous phase was washed with 100 mL CH2Cl2
  3. dry with materialthe combined organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a an oil that
  7. customproduced a stiff foam when

출처 및 근거

ORD 기록
ord-5c7a003d7dfd49e492a5a35dc8bfbd98
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096634B2

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