Phosphorus oxychloride → (R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine

HRID 81005

反応式

HRID 81005 の反応式
[CH3:1][C@H:2]1[C:10]2[C:9](O)=[N:8][CH:7]=[N:6][C:5]=2[CH2:4][CH2:3]1.O=P(Cl)(Cl)[Cl:14]>>[Cl:14][C:9]1[C:10]2[C@H:2]([CH3:1])[CH2:3][CH2:4][C:5]=2[N:6]=[CH:7][N:8]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178461168HCID 178461168、化合物

生成物 1

HCID 59670769(R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine収率 49%

実験手順

A mixture of (R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol (5.8 g, 38.62 mmol) in POCl3 (20 mL) was refluxed for 5 minutes. The excess POCl3 was removed under vacuum, and the residue was dissolved in DCM (50 mL). The mixture was then added to saturated NaHCO3 (200 mL). The aqueous phase was extracted with DCM (3×100 mL), and the combined organic phases were dried and concentrated. The residue was purified by silica gel chromatography, eluting with ethyl acetate to give (R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (3.18 g, 49%). 1H NMR (CDCl3, 400 MHz) δ 8.81 (s, 1H), 3.47 (m, 1H), 3.20 (m, 1H), 3.05 (m, 1H), 2.41 (m, 11H), 1.86 (m, 3H), 1.47 (m, 3H).

後処理

  1. temperaturewas refluxed for 5 minutes
  2. customThe excess POCl3 was removed under vacuum
  3. dissolutionthe residue was dissolved in DCM (50 mL)
  4. additionThe mixture was then added to saturated NaHCO3 (200 mL)
  5. extractionThe aqueous phase was extracted with DCM (3×100 mL)
  6. customthe combined organic phases were dried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-b57ccfeb121b45429c3a6adc65eca97f
出典データセット
uspto-grants-2014_09
特許番号
US08846683B2

関連ノート

読み込み中…