Phosphorus oxychloride → 2-Methyl-5-propyl-6-chloro-pyrimidine-4-carboxylic acid ethyl ester

HRID 916643Notes

Reaction equation

HRID 916643 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([CH2:12][CH2:13][CH3:14])=[C:10](O)[N:9]=[C:8]([CH3:16])[N:7]=1)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:19]>>[CH2:1]([O:3][C:4]([C:6]1[C:11]([CH2:12][CH2:13][CH3:14])=[C:10]([Cl:19])[N:9]=[C:8]([CH3:16])[N:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178439777HCID 178439777, compound

Product 1

HCID 233941042-Methyl-5-propyl-6-chloro-pyrimidine-4-carboxylic acid ethyl ester

Conditions

Temperature
85 °C

Procedure

A mixture of 121 (10 mmol) and POCl3 (25 ml) is heated at 85° C. for 4 hours. The solvent is removed in vacuo and EtOAc (40 ml) and water (30 ml) are added to the residue. NaHCO3 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 evaporated. Flash column purification of the residue with 3:1 EtOAc, hexane provides the product (122) as a light yellow oil.

Workup

  1. customThe solvent is removed in vacuo and EtOAc (40 ml) and water (30 ml)
  2. additionare added to the residue
  3. additionNaHCO3 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)
  8. customevaporated
  9. customFlash column purification of the residue with 3:1 EtOAc, hexane

Sources & evidence

ORD record
ord-373f08c2b5304eb88c7ce7cb3c5524b3
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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