3,4-dihydro-2H-pyran → 4-Chloro-7-[(1R)-1-methyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-7H-pyrrolo[2,3-d]pyrimidine

HRID 82143

반응식

HRID 82143 반응식
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[C:9]2[CH:16]=[CH:15][N:14]([C@H:17]([CH3:20])[CH2:18][OH:19])[C:10]=2[N:11]=[CH:12][N:13]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[Cl:7][C:8]1[C:9]2[CH:16]=[CH:15][N:14]([C@H:17]([CH3:20])[CH2:18][O:19][CH:6]3[CH2:5][CH2:4][CH2:3][CH2:2][O:1]3)[C:10]=2[N:11]=[CH:12][N:13]=1

참가 물질

5

반응물 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86672074(2R)-2-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)propan-1-ol

생성물 1

HCID 866720774-Chloro-7-[(1R)-1-methyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-7H-pyrrolo[2,3-d]pyrimidine수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2,3-Dihydropyran (25.0 mL, 270 mmol) was added to (2R)-2-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)propan-1-ol (11.00 g, 51.97 mmol) (see Preparation 3) and pyridinium toluene-4-sulphonate (3.92 g, 15.6 mmol) in DCM (150 mL). The reaction mixture was washed with water (200 mL) and the aqueous phase was extracted with DCM (2×150 mL). The combined organic phases were dried over magnesium sulfate and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (gradient of heptane:EtOAc 100:0 to 70:30) to afford the title compound as a yellow oil in 100% yield, 15.65 g.

후처리

  1. washThe reaction mixture was washed with water (200 mL)
  2. extractionthe aqueous phase was extracted with DCM (2×150 mL)
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe crude material was purified by column chromatography on silica gel (gradient of heptane:EtOAc 100:0 to 70:30)

출처 및 근거

ORD 기록
ord-b8bda83e3e5d4de991cd9b3d8df6adb2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

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