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

HRID 1485529ノート

反応式

HRID 1485529 の反応式
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

参加物

6

反応物 3

HCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 866710656-chloro-4-[(tetrahydro-2H-pyran-4-yl)oxy]-Pyrido[3,2-d]pyrimidine2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-76e2c28105f74cb4bb57fe97be8ccd3c
出典データセット
uspto-grants-2016_08
特許番号
US09422298B2

反応ノート

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