2-Methylpentane → 6-Carbamoyl-2-chloro-4-[5-(3-fluoro-5-morpholinobenzamido)-2-methylanilino]-pyrimidine

HRID 1760960Notes

Reaction equation

HRID 1760960 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:24])[C:11]2[CH:16]=[C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:14]=[C:13]([F:23])[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[C:25]([C:28]1[N:33]=[C:32]([Cl:34])[N:31]=[C:30](Cl)[CH:29]=1)(=[O:27])[NH2:26].C(N(CC)C(C)C)(C)C.CCCC(C)C>O.C(O)CCC>[C:25]([C:28]1[N:33]=[C:32]([Cl:34])[N:31]=[C:30]([NH:1][C:2]2[CH:3]=[C:4]([NH:9][C:10](=[O:24])[C:11]3[CH:16]=[C:15]([N:17]4[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)[CH:14]=[C:13]([F:23])[CH:12]=3)[CH:5]=[CH:6][C:7]=2[CH3:8])[CH:29]=1)(=[O:27])[NH2:26]

Participants

7

Reactant 4

HCID 78922-MethylpentaneHCID 81531DiisopropylethylamineHCID 2411282,6-Dichloropyrimidine-4-carboxamideHCID 11450304N-(3-amino-4-methylphenyl)-3-fluoro-5-morpholinobenzamide

Product 1

HCID 99132266-Carbamoyl-2-chloro-4-[5-(3-fluoro-5-morpholinobenzamido)-2-methylanilino]-pyrimidineYield 12.1%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A mixture of N-(3-amino-4-methylphenyl)-3-fluoro-5-morpholinobenzamide (0.33 g), 6-carbamoyl-2,4-dichloropyrimidine (0.212 g), N,N-di-isopropylethylamine (0.53 ml) and n-butanol (5 ml) was stirred and heated to reflux for 36 hours. Water and isohexane were added and the precipitated product was isolated and dried. There was thus obtained the title compound (0.059 g); NMR Spectrum: (DMSOd6) 2.14 (s, 3H), 3.23 (m, 4H), 3.72 (m, 4H), 6.97 (d, 1H), 7.12 (d, 1H), 7.29 (m, 2H), 7.6 (d, 1H), 7.74 (s, 1H), 7.81 (s, 1H), 7.92 (s, 1H), 9.9 (s, 1H), 10.21 (s, 1H); Mass Spectrum: M−H′ 483 & 485.

Workup

  1. temperatureheated
  2. temperatureto reflux for 36 hours
  3. customthe precipitated product was isolated
  4. customdried

Sources & evidence

ORD record
ord-502dd877952742f0bb9e74b76ddf062d
Source dataset
uspto-grants-2005_01
Patent number
US06846827B1

Reaction notes

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