Diisopropylethylamine → N-(5-tert-butyl-2-methylphenyl)-5-fluoro-2-[4-(1H-1,2,3-triazol-1-yl)piperidin-1-yl]pyrimidin-4-amine

HRID 888997Notes

Reaction equation

HRID 888997 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:20])=[C:9]([NH:11][C:12]2[C:17]([F:18])=[CH:16][N:15]=[C:14](Cl)[N:13]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N:21]1([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:25]=[CH:24][N:23]=[N:22]1.C(N(C(C)C)CC)(C)C>CC(O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:20])=[C:9]([NH:11][C:12]2[C:17]([F:18])=[CH:16][N:15]=[C:14]([N:29]3[CH2:28][CH2:27][CH:26]([N:21]4[CH:25]=[CH:24][N:23]=[N:22]4)[CH2:31][CH2:30]3)[N:13]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 190060194-(1H-1,2,3-Triazol-1-YL)piperidineHCID 59191944N-(5-tert-butyl-2-methylphenyl)-2-chloro-5-fluoropyrimidin-4-amine

Product 1

HCID 59191957N-(5-tert-butyl-2-methylphenyl)-5-fluoro-2-[4-(1H-1,2,3-triazol-1-yl)piperidin-1-yl]pyrimidin-4-amineYield 34.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of the product of Step 1 (123 mg, 0.42 mmol), 4-(1H-1,2,3-triazol-1-yl)piperidine (94 mg, 0.50 mmol) and diisopropylethylamine (2 mL) was irradiated in 2-propanol (2 mL), in a microwave oven, at 150° C. for 2 h. The mixture was cooled and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40S, eluting with EtOAc/hexane (0%-100%) to give the product (59 mg, 34%) as a solid.

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel Biotage 40S
  4. washeluting with EtOAc/hexane (0%-100%)

Sources & evidence

ORD record
ord-e3ad2da433b0470997d0757545dad0c1
Source dataset
uspto-grants-2012_08
Patent number
US08252803B2

Reaction notes

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