Phosphorus oxychloride → 7-Chloro-1-methyl-2,3-dihydroimidazo[1,2-C]pyrimidin-5(1H)-one

HRID 873039Notes

Reaction equation

HRID 873039 reaction equation
[CH3:1][N:2]1[C:10]2[N:5]([C:6](=[O:12])[NH:7][C:8](=O)[CH:9]=2)[CH2:4][CH2:3]1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:8]1[CH:9]=[C:10]2[N:2]([CH3:1])[CH2:3][CH2:4][N:5]2[C:6](=[O:12])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 596353557-Hydroxy-1-methyl-2,3-dihydroimidazo[1,2-C]pyrimidin-5(1H)-one

Product 1

HCID 717434587-Chloro-1-methyl-2,3-dihydroimidazo[1,2-C]pyrimidin-5(1H)-oneYield 93%

Conditions

Temperature
90 °C

Procedure

A suspension of 1-methyl-2,3-dihydroimidazo[1,2-c]pyrimidine-5,7(1H,6H)-dione (0.41 g, 2.45 mmol) in POCl3 (15 mL, 161 mmol) was stirred at 90° C. for 6 h. The suspension was concentrated in vacuo to remove all of POCl3. Cold water was added to the resultant residue, and then solid NaOH was added dropwise to adjust pH to ˜12. The solution was stirred at rt for 2 h. Aqueous HCl was added to adjust pH to ˜7. Purification via Mass Directed AutoPrep (MDAP) afforded the title compound as a white solid (0.42 g, 93% yield).

Workup

  1. concentrationThe suspension was concentrated in vacuo
  2. customto remove all of POCl3
  3. additionCold water was added to the resultant residue
  4. additionsolid NaOH was added dropwise
  5. stirringThe solution was stirred at rt for 2 h
  6. additionAqueous HCl was added
  7. customPurification via Mass Directed AutoPrep (MDAP)

Sources & evidence

ORD record
ord-6edbe48d189a4e85ba5c21341ca5d47b
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

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