Potassium Carbonate → 5-bromo-N-(2-(4-fluorophenyl)-2-methylpropyl)pyrimidin-2-amine

HRID 1853117Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][C:5](F)=[N:6][CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:20])([CH3:19])[CH2:17][NH2:18])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:18][CH2:17][C:16]([C:13]2[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=2)([CH3:20])[CH3:19])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 5-bromo-2-fluoropyrimidine (1.0 g, 5.6 mmol, 1.0 equiv) and 2-(4-fluorophenyl)-2-methylpropan-1-amine (1.05 g, 6.3 mmol. 1.1 equiv) in isopropanol (12 mL) in a microwave vial equipped with a stir bar was added potassium carbonate (3.68 g, 11.2 mmol, 2.0 equiv). The vial was fitted with a microwave vial cap and heated to 120° C. for 45 min. The reaction mixture was filtered to remove the solid potassium carbonate and concentrated in vacuo. After the residue was redissolved in EtOAc and water, the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification by silica gel chromatography (3%-5% MeOH/DCM) provided the title compound as a yellow solid (1.15 g, 65%), (m/z [M+H]=324.2).

Workup

customThe vial was fitted with a microwave
customvial cap
filtrationThe reaction mixture was filtered
customto remove the solid potassium carbonate
concentrationconcentrated in vacuo
dissolutionAfter the residue was redissolved in EtOAc
washwater, the organic layer was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customPurification by silica gel chromatography (3%-5% MeOH/DCM)

Sources & evidence

ORD record: ord-9dd61d3147e04ea79f93d79345ba3dc7
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962632B2

Reaction notes

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