Methanol → 6-Chloro-5-fluoro-2-methylpyrimidin-4-amine

HRID 1663461Notes

Reaction equation

HRID 1663461 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6](Cl)[N:5]=[C:4]([CH3:10])[N:3]=1.[OH-].[NH4+:12].CO>O>[NH2:12][C:6]1[C:7]([F:8])=[C:2]([Cl:1])[N:3]=[C:4]([CH3:10])[N:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 137310334,6-Dichloro-5-fluoro-2-methylpyrimidine

Product 1

HCID 552836246-Chloro-5-fluoro-2-methylpyrimidin-4-amineYield 61.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Part C: A mixture of 4,6-dichloro-5-fluoro-2-methylpyrimidine (1.55 g, 8.56 mmol), ammonium hydroxide (35%, 10.0 mL, 257 mmol), and MeOH (1.00 mL) was heated, in a sealed tube, at 70° C. for 2 h. The reaction mixture was cooled to RT, and a precipitate was formed. The reaction mixture was diluted with water (ca. 10 mL) and was stirred 30 min. The solids were collected by suction filtration, washed with water and air-dried to give 4-amino-6-chloro-5-fluoro-2-methylpyrimidine (845 mg, 61%) as a tan solid. LCMS (m/z): 162,164 (M+H)+

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customa precipitate was formed
  3. filtrationThe solids were collected by suction filtration
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-69b02f7e6dba457ab58b732d0aef4f6b
Source dataset
uspto-grants-2011_10
Patent number
US08034954B2

Reaction notes

Loading…