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

HRID 1621364Notes

Reaction equation

HRID 1621364 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>[Cl:1][C:2]1[N:3]=[C:4]([CH3:10])[N:5]=[C:6]([NH2:12])[C:7]=1[F:8]

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 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4,6-dichloro-5-fluoro-2-methylpyrimidine (1.55 g, 8.6 mmol) in aqueous ammonium hydroxide (10.00 mL, 90 mmol) and MeOH (1.00 mL, 25 mmol) was heated at 70° C. for 2 h (sealed tube). After cooling, 10 mL water was added and stirred for 30 min. The solid was isolated, washed with water, and dried to give the desired product 6-chloro-5-fluoro-2-methylpyrimidin-4-amine (0.9244 g, 67%) as a white solid. MS (API-ES) m/z 163 (M+H)+.

Workup

  1. custom(sealed tube)
  2. temperatureAfter cooling
  3. customThe solid was isolated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5ed149a1a7f747959fc6ec1f49f1390e
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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