Hydrochloric Acid → 6-chloro-5-methyl-N-phenylpyrimidin-4-amine

HRID 241004

Reaction equation

HRID 241004 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C(O)(C)C>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 8188604,6-Dichloro-5-methylpyrimidine

Product 1

HCID 637349086-chloro-5-methyl-N-phenylpyrimidin-4-amineYield 85.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 4,6-dichloro-5-methylpyrimidine (2.27 g, 13.9 mmol) and aniline (1.0 g, 10.7 mmol) in isopropanol (15 mL) was added concentrated aqueous hydrochloric acid (1.5 mL) and heated to reflux for 2.5 h. The mixture was then concentrated and the residue triturated with ethyl acetate:isopropanol 4:1. The solid was collected by filtration and washed with additional ethyl acetate:isopropanol 4:1 then dried to give 6-chloro-5-methyl-N-phenylpyrimidin-4-amine (2.0 g, 67% yield). 1H NMR (400 MHz, d6-DMSO): 8.85 (s, 1H), 8.26 (s, 1H), 7.60 (d, 2H), 7.35 (tr, 2H), 7.11 (tr, 1H), 2.31 (s, 3H). MS (EI) for C11H10ClN3: 220 (MH+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2.5 h
  3. concentrationThe mixture was then concentrated
  4. customthe residue triturated with ethyl acetate:isopropanol 4:1
  5. filtrationThe solid was collected by filtration
  6. washwashed with additional ethyl acetate:isopropanol 4:1
  7. customthen dried

Sources & evidence

ORD record
ord-22761ad4d6464744adf8f3738e887d43
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Linked notes

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