Sodium Hydroxide → 2-Butylamino-4-chloro-6-methylpyrimidine

HRID 1588484Notes

Reaction equation

HRID 1588484 reaction equation
[CH2:1]([NH:5][C:6]1[NH:11][C:10](=O)[CH:9]=[C:8]([CH3:13])[N:7]=1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:16])=O.[OH-].[Na+]>O>[CH2:1]([NH:5][C:6]1[N:11]=[C:10]([Cl:16])[CH:9]=[C:8]([CH3:13])[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride2×HCID 135773302HCID 135773302, compound

Product 1

HCID 197920702-Butylamino-4-chloro-6-methylpyrimidineYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Butylamino-6-methylpyrimidin-4-one (8.4 g, 0.046M) was treated with phosphorus oxychloride (5 ml). A vigorous reaction ensued. When this had subsided, the resultant mixture was heated at 90° C. for 30 minutes. This gave an orange coloured syrup which was cooled and added to water to decompose the excess phosphorus oxychloride. The aqueous solution was adjusted to pH 7 using 2M sodium hydroxide solution. The resultant white precipitate was extracted with methylene chloride. The extracts were dried (MgSO4) and the solvent evaporated to give 2-butylamino-4-chloro-6-methylpyrimidine (8.1 g) as a solid, m.p. 35°-36° C., in 88% yield.

Workup

  1. customThis gave an orange coloured syrup which
  2. temperaturewas cooled
  3. extractionThe resultant white precipitate was extracted with methylene chloride
  4. dry with materialThe extracts were dried (MgSO4)
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-59031d32267642c49617c848c90d2358
Source dataset
uspto-grants-1993_06
Patent number
US05223505

Reaction notes

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