Allylamine → HCID 22594092, compound

HRID 1760970Notes

Reaction equation

HRID 1760970 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:19]=3)=[O:17])[CH:12]=[CH:11][C:10]=2[CH3:30])[CH:5]=[CH:4][N:3]=1.[CH2:31]([NH2:34])[CH:32]=[CH2:33]>>[CH2:31]([NH:34][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)[CH:19]=3)=[O:17])[CH:12]=[CH:11][C:10]=2[CH3:30])[CH:5]=[CH:4][N:3]=1)[CH:32]=[CH2:33]

Participants

3

Reactant 2

HCID 7853AllylamineHCID 9867061HCID 9867061, compound

Product 1

HCID 22594092HCID 22594092, compound

Procedure

A mixture of 2-chloro-4-[2-methyl-5-(2-morpholinopyrid-4-ylcarbonylamino)anilino]pyrimidine (0.2 g) and allylamine (0.4 ml) was stirred and heated to reflux for 18 hours. The mixture was evaporated and the residue was purified by column chromatography on silica using a 9:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound as a solid (0.135 g); NMR Spectrum: (DMSOd6) 2.17 (s, 3H), 3.5 (m, 4H), 3.7 (m, 4H), 3.82 (m, 2H), 4.95 (m, 1H), 5.05 (m, 1H), 5.85 (m, 2H), 6.57 (br m, 1H), 7.07 (m, 1H), 7.17 (m, 2H), 7.43 (m, 1H), 7.78 (m, 1H), 7.87 (br m, 1H), 8.24 (m, 1H), 8.37 (s, 1H), 10.18 (s, 1H); Mass Spectrum: M+H+ 446.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. customThe mixture was evaporated
  4. customthe residue was purified by column chromatography on silica using
  5. additiona 9:1 mixture of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-da018097b5d141d5923601f7956cab17
Source dataset
uspto-grants-2005_01
Patent number
US06846827B1

Reaction notes

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