Diisopropylethylamine → HCID 67452341, compound

HRID 1474092Notes

Reaction equation

HRID 1474092 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:23])([CH3:22])[CH2:20][NH2:21])=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([CH3:23])([CH3:22])[CH2:20][NH:21][C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12627752Methyl 2-chloropyrimidine-5-carboxylateHCID 212510232-(4-Fluorophenyl)-2-methylpropan-1-amine

Product 1

HCID 67452341HCID 67452341, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a 20 dram vial was added methyl 2-chloropyrimidine-5-carboxylate (250 mg, 1.4 mmol, 1.0 equiv), 2-(4-fluorophenyl)-2-methylpropan-1-amine (468 mg, 2.8 mmol, 2.0 equiv), DIPEA (1.0 mL, 5.6 mmol, 4.0 equiv), and toluene (5 mL). The vial was heated in an oil bath to 60° C. and stirred for 20 min, concentrated, and purified by silica gel column chromatography (0-50% EtOAc/hexanes) to give 325 mg (77%) of methyl 2-(2-(4-fluorophenyl)-2-methylpropylamino)pyrimidine-5-carboxylate as a white solid (m/z [M+H]=304.1).

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel column chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ab169e8727f844da86292338d1c591b9
Source dataset
uspto-grants-2015_04
Patent number
US09018223B2

Reaction notes

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