m-Toluidine → Methyl 2-chloro-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate

HRID 515952

Reaction equation

HRID 515952 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:4]([CH3:13])[N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=1.C(N(C(C)C)C(C)C)C>CC#N.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([CH3:13])[C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:6]([NH:14][C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[N:7]=1

Participants

6

Reactant 3

HCID 7934m-ToluidineHCID 81531DiisopropylethylamineHCID 57531614Methyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate

Product 1

HCID 58317549Methyl 2-chloro-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate (940 mg, 4.25 mmol), m-toluidine (0.461 mL, 4.25 mmol) and N-ethyldiisopropylamine (1.481 mL, 8.51 mmol) in CH3CN (30 mL) was heated under reflux for 3 h. The mixture was diluted with EtOAc, and was washed with brine and water. The organic extract was dried and concentrated under reduced pressure to give the title compound as a light yellow solid (1.2 g, 97%). [M+H] calc'd for C14H14N3ClO2, 292; found, 292.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. washwas washed with brine and water
  4. extractionThe organic extract
  5. customwas dried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a1eb3af0b1443d4b20b1064e6aa8b43
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Linked notes

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