Phosphorus oxychloride → 4-Chloro-2-cyclopropylpyrimidine

HRID 572448Notes

Reaction equation

HRID 572448 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH:6]1([C:9]2[N:14]=[C:13](O)[CH:12]=[CH:11][N:10]=2)[CH2:8][CH2:7]1>>[Cl:3][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([CH:6]2[CH2:8][CH2:7]2)[N:14]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1785164792-Cyclopropylpyrimidin-4-ol

Product 1

HCID 249037134-Chloro-2-cyclopropylpyrimidine

Conditions

Temperature
150 °C

Procedure

POCl3 (5 mL) was added to 2-cyclopropylpyrimidin-4-ol (100 mg, 0.735 mmol) and refluxed at 150° C. for 2.5 hours. The resulting mixture was concentrated, the concentrate was basified with dilute sodium bicarbonate solution and diluted with DCM. The organic layer was washed with brine, dried over sodium sulphate and concentrated to afford 125 mg of the crude product as a pale brown liquid.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additiondiluted with DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f34f3d6bbc604d95bedec43436bb69ca
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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