Diisopropylethylamine → HCID 22594119, compound

HRID 1760977Notes

Reaction equation

HRID 1760977 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][C:16](=[O:29])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[CH:18]=3)[CH:12]=[CH:11][C:10]=2[CH3:30])[CH:5]=[CH:4][N:3]=1.C[NH:32][CH2:33][CH2:34][CH:35]1[CH2:39][CH2:38][CH2:37][NH:36]1.[CH:40](N(CC)C(C)C)(C)C>C(O)CCC>[CH3:30][C:10]1[CH:11]=[CH:12][C:13]([NH:15][C:16](=[O:29])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:18]=2)=[CH:14][C:9]=1[NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:32][CH2:33][CH2:34][CH:35]2[CH2:39][CH2:38][CH2:37][N:36]2[CH3:40])[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 20977074HCID 20977074, compoundHCID 22594104HCID 22594104, compound

Product 1

HCID 22594119HCID 22594119, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-4-[2-methyl-5-(3-morpholinobenzamido)anilino]pyrimidine (0.64 g), 2-(N-methylpyrrolidin-2-ylethylamine (0.44 ml), N,N-di-isopropylethylamine (0.52 ml) and n-butanol (7 ml) was stirred and heated to 100° C. for 18 hours. The mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent followed by increasingly polar mixtures of methylene chloride and methanol containing 1% aqueous ammonium hydroxide solution. There was thus obtained the title compound as a solid (0.33 g); NMR Spectrum: (DMSOd6) 1.44 (m, 2H), 1.62 (m, 2H), 1.88 (m, 2H), 2.15 (s, 3H), 2.31 (m, 4H), 3.04 (m, 2H), 3.17 (m, 5H), 3.74 (m, 4H), 5.88 (d, 1H), 6.5 (m, 1H), 7.13 (m, 2H), 7.34 (m, 2H), 7.44 (m, 2H), 7.77 (d, 1H), 7.9 (m, 1H), 8.37 (s, 1H), 10.04 (s, 1H); Mass Spectrum: M+H+ 516.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography on silica using
  3. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  4. temperatureby increasingly polar mixtures of methylene chloride and methanol containing 1% aqueous ammonium hydroxide solution

Sources & evidence

ORD record
ord-a165db4ea89148268b2d7b74f3b2144f
Source dataset
uspto-grants-2005_01
Patent number
US06846827B1

Reaction notes

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