Phosphorus oxychloride → 5-(2-Benzyloxy-ethyl)-4-chloro-6-methyl-pyrimidine

HRID 916656Notes

Reaction equation

HRID 916656 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[C:12](O)=[N:13][CH:14]=[N:15][C:16]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:21]>>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[C:12]([Cl:21])=[N:13][CH:14]=[N:15][C:16]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178433211HCID 178433211, compound

Product 1

HCID 575033065-(2-Benzyloxy-ethyl)-4-chloro-6-methyl-pyrimidine

Conditions

Temperature
100 °C

Procedure

A mixture of 160 (4.1 g, 17 mmol) and POCl3 (10 ml) is heated at 100° C. for 3 hours. The solvent is removed in vacuo and EtOAc (30 ml) and water (30 ml) are added to the residue. NaHCO3 (aq.) is carefully added until the pH of the aqueous layer is greater than 7. The layers are separated and the aqueous layer is extracted with EtOAc (2×30 ml). The combined extracts are washed with brine (50 ml), dried (Na2SO4) and solvent evaporated. Flash column purification of the residue (EtOAc:hexane=1:2) provides the product (161) as a light yellow oil.

Workup

  1. customThe solvent is removed in vacuo and EtOAc (30 ml) and water (30 ml)
  2. additionare added to the residue
  3. additionNaHCO3 (aq.) is carefully added until the pH of the aqueous layer
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with EtOAc (2×30 ml)
  6. washThe combined extracts are washed with brine (50 ml)
  7. dry with materialdried (Na2SO4) and solvent
  8. customevaporated
  9. customFlash column purification of the residue (EtOAc:hexane=1:2)

Sources & evidence

ORD record
ord-75b33cc552fe4de9a9172e78d7782f42
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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