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

HRID 81005

반응식

HRID 81005 반응식
[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

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178461168HCID 178461168, 화합물

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b57ccfeb121b45429c3a6adc65eca97f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846683B2

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