Isopropylamine → HCID 22594090, compound

HRID 1760972Notes

Reaction equation

HRID 1760972 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.[CH:31]([NH2:34])([CH3:33])[CH3:32]>>[CH: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)([CH3:33])[CH3:32]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 9867061HCID 9867061, compound

Product 1

HCID 22594090HCID 22594090, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-4-[2-methyl-5-(2-morpholinopyrid-4-ylcarbonylamino)anilino]pyrimidine (0.2 g) and isopropylamine (5 ml) was heated to 100° C. in a sealed tube for 24 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and water. The organic phase was washed with brine, dried over sodium sulphate and evaporated. The resultant solid was recrystallised from tert-butyl methyl ether to give the title compound (0.145 g); NMR Spectrum: (DMSOd6) 1.04 (s, 3H), 1.06 (s, 3H), 2.17 (s, 3H), 3.5 (m, 4H), 3.7 (m, 4H), 3.97 (m, 1H), 5.82 (m, 1H), 6.2 (br m, 1H), 7.07 (m, 1H), 7.19 (m, 2H), 7.45 (m, 1H), 7.78 (m, 1H), 7.87 (br m, 1H), 8.25 (m, 1H), 8.31 (s, 1H), 10.18 (s, 1H); Mass Spectrum: M+H+ 448.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between methylene chloride and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe resultant solid was recrystallised from tert-butyl methyl ether

Sources & evidence

ORD record
ord-7c7b9f3d6f714248ab54973f560de017
Source dataset
uspto-grants-2005_01
Patent number
US06846827B1

Reaction notes

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