Diisopropylethylamine → HCID 86592615, compound

HRID 968566Notes

Reaction equation

HRID 968566 reaction equation
C(N(C(C)C)CC)(C)C.C([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(C)(C)C.[C:21]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32]2[C:33]3[CH:42]=[CH:41][C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=4[C:49]([F:52])([F:51])[F:50])=[N:39][C:34]=3[N:35]=[C:36]([Cl:38])[N:37]=2)=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22]>C(#N)C>[C:21]([C:25]1[CH:26]=[CH:27][C:28]([NH:31][C:32]2[C:33]3[CH:42]=[CH:41][C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=4[C:49]([F:52])([F:51])[F:50])=[N:39][C:34]=3[N:35]=[C:36]([Cl:38])[N:37]=2)=[CH:29][CH:30]=1)([CH3:24])([CH3:22])[CH3:23].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 254260N-(1,1-Dimethylethyl)benzenamineHCID 22030367HCID 22030367, compound

Product 1

HCID 86592615HCID 86592615, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of diisopropylethylamine (260 mg, 2.0 mmol) in acetonitrile (5 mL), add t-butylaniline (124 mg, 1.0 mmol) followed by (4-tert-Butyl-phenyl)-[2-chloro-7-(2-trifluoromethyl-phenyl)-pyrido[2,3-d]pyrimidin-4-yl]-amine (310 mg, 1.0 mmol). Heat the mixture to 80° C. for six hours. Evaporate the solvent, and partition between 1M NaOH and EtOAc. Dry the solvent (Na2SO4) and evaporate. Purify by silica gel chromatography (1:1 hexanes/EtOAc to furnish the monoaniline (4-tert-Butyl-phenyl)-[2-chloro-7-(2-trifluoromethyl-phenyl)-pyrido[2,3-d]pyrimidin-4-yl]-amine as a yellow solid.

Workup

  1. customEvaporate the solvent
  2. custompartition between 1M NaOH and EtOAc
  3. dry with materialDry the solvent (Na2SO4)
  4. customevaporate
  5. customPurify by silica gel chromatography (1:1 hexanes/EtOAc

Sources & evidence

ORD record
ord-eec1e97defeb4257b03f0a910b756ff5
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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