Cyclopentanol → 6-chloro-4-(cyclopentyloxy)-Pyrido[3,2-d]pyrimidine

HRID 1485529노트

반응식

HRID 1485529 반응식
C1(O)CCCC1.[H-].[Na+].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[N:14]=[CH:15][N:16]=[C:17]([O:20][CH:21]3[CH2:26][CH2:25]O[CH2:23][CH2:22]3)[C:18]=2[N:19]=1>CN(C=O)C.O>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[N:14]=[CH:15][N:16]=[C:17]([O:20][CH:21]3[CH2:26][CH2:25][CH2:23][CH2:22]3)[C:18]=2[N:19]=1

참가 물질

6

반응물 3

HCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 866710656-chloro-4-[(tetrahydro-2H-pyran-4-yl)oxy]-Pyrido[3,2-d]pyrimidine2회

생성물 1

HCID 866710716-chloro-4-(cyclopentyloxy)-Pyrido[3,2-d]pyrimidine수율 32%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of cyclopentanol (0.050 ml, 0.550 mmol) in DMF (2.500 ml) was added NaH (0.026 g, 55% dispersion in mineral oil, 0.600 mmol) at 0° C. The reaction mixture was stirred for 30 min. at room temperature, 4,6-dichloropyrido[3,2-d]pyrimidine (Intermediate 1, step D) (0.1 g, 0.500 mmol) was added to the mixture at 0° C. After being stirred for 2 hours at room temperature, the reaction mixture was diluted with water, and extracted with EtOAc. The organic layers were dried over MgSO4 filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=5:1) to give 6-chloro-4-(cyclopentyloxy)pyrido[3,2-d]pyrimidine (0.04 g, 32%) as a yellow solid. 1H-NMR (CDCl3, Varian 400 MHz): δ 1.63-1.74 (2H, m), 1.86-1.96 (2H, m), 1.99-2.07 (2H, m), 2.12-2.20 (2H, m), 5.72-5.77 (1H, m), 7.72 (1H, d, J=8.8 Hz), 8.18 (1H, d, J=8.8 Hz), 8.83 (1H, s).

후처리

  1. stirringAfter being stirred for 2 hours at room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on SiO2 (Hex:EtOAc=5:1)

출처 및 근거

ORD 기록
ord-76e2c28105f74cb4bb57fe97be8ccd3c
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422298B2

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