Phosphorus oxychloride → Methyl 4-((2-amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-fluorobenzoate

HRID 2387815Notes

Reaction equation

HRID 2387815 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](O)[C:5]([CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=2[F:20])=[C:4]([CH3:21])[N:3]=1.P(Cl)(Cl)([Cl:24])=O>>[NH2:1][C:2]1[N:7]=[C:6]([Cl:24])[C:5]([CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=2[F:20])=[C:4]([CH3:21])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178497677HCID 178497677, compound

Product 1

HCID 86633399Methyl 4-((2-amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-fluorobenzoate

Conditions

Temperature
90 °C

Procedure

The product from step (ii) (6.6 g) was added to phosphorous oxychloride (40 ml) under nitrogen. The resulting mixture was stirred at 90° C. for 15 h. The phosphorous oxychloride was evaporated under reduced pressure and the residue cautiously diluted with water (50 mL). The aqueous phase was neutralised with NaHCO3 and heated at 50° C. for 1 h. The mixture was allowed to cool and the precipitate was collected by filtration. The solid was suspended in MeCN (40 mL) and collected by filtration to give the subtitle compound as a cream solid 3.70 g that was used without further purification.

Workup

  1. customThe phosphorous oxychloride was evaporated under reduced pressure
  2. additionthe residue cautiously diluted with water (50 mL)
  3. temperatureheated at 50° C. for 1 h
  4. temperatureto cool
  5. filtrationthe precipitate was collected by filtration
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-0ccf766543b84b0a9b176650ac04944a
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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