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

HRID 1617161Notes

Reaction equation

HRID 1617161 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-43dd9379069c44baa2a9792e6ce0b9dd
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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