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

HRID 911820Notes

Reaction equation

HRID 911820 reaction equation
[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

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178461168HCID 178461168, compound

Product 1

HCID 59670769(R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidineYield 44%

Procedure

The solution of (R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol (2.08 g, 13.9 mmol) in POCl3 (10 ml) was refluxed for 2 hours. After cooling, the excess POCl3 was evaporated and the residue was dissolved in CH2Cl2 (50 ml) and was neutralized with saturated NaHCO3. The aqueous phase was extracted with CH2Cl2. The organic phase was dried and concentrated. The residue purified on silica gel (20% EtOAc in hexanes) to afford the title compound (1.0 g, 44% yield).

Workup

  1. temperatureAfter cooling
  2. customthe excess POCl3 was evaporated
  3. dissolutionthe residue was dissolved in CH2Cl2 (50 ml)
  4. extractionThe aqueous phase was extracted with CH2Cl2
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customThe residue purified on silica gel (20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-92f6f17f1877430291e1b3e1cdaf8fff
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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