Aniline → HCID 86747976, compound

HRID 1728551Notes

Reaction equation

HRID 1728551 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([Cl:13])[N:5]=[C:4]([CH3:14])[N:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[NH:15]([C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([Cl:13])[N:5]=[C:4]([CH3:14])[N:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 19071353HCID 19071353, compound

Product 1

HCID 86747976HCID 86747976, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4,6-dichloro-2-methylpyrimidine-5-acetic acid, methyl ester (8.5g, 36mM) and aniline (4.7g, 49mM) was heated at 50° C. for 13 hours. Methylene chloride (300ml) was added to the cooled mixture and the mixture filtered. The liltrate was washed with 2M hydrochloric acid (1×170ml, 1×85ml) and water. The organic layer was separated, stirred with 2M sodium hydroxide (110ml) and then separated. The aqueous layer was extracted with methylene chloride (2×85ml). The organic layers were combined, washed with water, over anhydrous magnesium sulphate and the solvent evaporated to afford a solid. This solid was purified by flash column chromatography on silica (Merck 9385), eluting with ethyl acetate/hexane (20:80 v/v) to give 4-anilino-6-chloro-2-methylpyrimidine-5-acetic acid, methyl ester (3.92g, 48.6%), m.p. 115°-116° C.; microanalysis, found; C,57.7; H, 4.5; N, 14.2%; C14H14N302. requires C, 57.6; H, 4.8; N, 14.4%; NMR: 2.53(3H,s,2-CH3), 3.79(3H,s, COOCH3), 3.80(2H,s,CH2), 7.05-7.65(5H, complex, aromatic), 7.9-8.0 (1H, broad,N--H).

Workup

  1. filtrationthe mixture filtered
  2. washThe liltrate was washed with 2M hydrochloric acid (1×170ml, 1×85ml) and water
  3. customThe organic layer was separated
  4. customseparated
  5. extractionThe aqueous layer was extracted with methylene chloride (2×85ml)
  6. washwashed with water, over anhydrous magnesium sulphate
  7. customthe solvent evaporated
  8. customto afford a solid
  9. customThis solid was purified by flash column chromatography on silica (Merck 9385)
  10. washeluting with ethyl acetate/hexane (20:80 v/v)

Sources & evidence

ORD record
ord-e71a3c69e2d94133b23f5a25fe2095a7
Source dataset
uspto-grants-1994_07
Patent number
US05328910

Reaction notes

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