Phosphorus oxychloride → 1-(4-Chloropyrimidin-2-yl)pyrrolidin-3-ol

HRID 386101Notes

Reaction equation

HRID 386101 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11](O)[CH:10]=[CH:9][N:8]=2)[CH2:3]1.O=P(Cl)(Cl)[Cl:16]>CN(C=O)C>[Cl:16][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([N:4]2[CH2:5][CH2:6][CH:2]([OH:1])[CH2:3]2)[N:12]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516515HCID 178516515, compound

Product 1

HCID 457875341-(4-Chloropyrimidin-2-yl)pyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(3-hydroxypyrrolidin-1-yl)pyrimidin-4-ol (4.0 g, 23 mol) in DMF (50 mL) was added POCl3 (4.2 g, 27 mmol). The reaction mixture was stirred at 50° C. for 2 hours. The reaction mixture was poured into 200 mL ice-water. The resulting solution was concentrated at 60° C. under vacuum. The residue was purified by acidic reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier) to afford the title compound.

Workup

  1. concentrationThe resulting solution was concentrated at 60° C. under vacuum
  2. customThe residue was purified by acidic reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier)

Sources & evidence

ORD record
ord-8e235af0624d4d90814a8d34561fd458
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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