N-Methylallylamine → HCID 22594093, compound

HRID 1760971Notes

Reaction equation

HRID 1760971 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]([NH:34][CH3:35])[CH:32]=[CH2:33]>>[CH2:31]([N: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[CH2:29][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)[CH3:35])[CH:32]=[CH2:33]

Participants

3

Reactant 2

HCID 69391N-MethylallylamineHCID 9867061HCID 9867061, compound

Product 1

HCID 22594093HCID 22594093, compound

Conditions

Temperature
75 °C

Procedure

A mixture of 2-chloro-4-[2-methyl-5-(2-morpholinopyrid-4-ylcarbonylamino)anilino]pyrimidine (0.2 g) and N-allyl-N-methylamine (0.25 ml) was stirred and heated to 75° C. for 3 hours. The mixture was cooled to ambient temperature and purified by column chromatography on silica using a 9:1 mixture of methylene chloride and methanol as eluent. The resultant oil was triturated under a mixture of isohexane and diethyl ether. There was thus obtained the title compound as a solid (0.055 g); NMR Spectrum: (DMSOd6) 2.17 (s, 3H), 2.95 (s, 3H), 3.5 (m, 4H), 3.7 (m, 4H), 4.1 (d, 2H), 5.04 (m, 2H), 5.75 (m, 1H), 5.91 (m, 1H), 7.07 (m, 1H), 7.17 (m, 2H), 7.19 (m, 1H), 7.86 (m, 1H), 7.98 (m, 1H), 8.25 (m, 1H), 8.42 (s, 1H), 10.17 (s, 1H); Mass Spectrum: M+H+ 460.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompurified by column chromatography on silica using
  3. additiona 9:1 mixture of methylene chloride and methanol as eluent
  4. customThe resultant oil was triturated under a mixture of isohexane and diethyl ether

Sources & evidence

ORD record
ord-99510d9857ce4fb49d85d6de62eddccc
Source dataset
uspto-grants-2005_01
Patent number
US06846827B1

Reaction notes

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