Potassium Carbonate → 5-chloro-6-((4-fluorobenzyl)oxy)-3-(5-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-2-methylphenyl)-2-methylpyrimidin-4(3H)-one

HRID 2172600Notes

Reaction equation

[Cl:1][C:2]1[C:3](=[O:29])[N:4]([C:18]2[CH:23]=[C:22]([C:24](=O)[C:25]#[CH:26])[CH:21]=[CH:20][C:19]=2[CH3:28])[C:5]([CH3:17])=[N:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.Cl.[OH:31][C:32]([CH3:37])([CH3:36])[C:33]([NH2:35])=[NH:34].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[C:3](=[O:29])[N:4]([C:18]2[CH:23]=[C:22]([C:24]3[CH:25]=[CH:26][N:35]=[C:33]([C:32]([OH:31])([CH3:37])[CH3:36])[N:34]=3)[CH:21]=[CH:20][C:19]=2[CH3:28])[C:5]([CH3:17])=[N:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 5-chloro-6-(4-fluoro-benzyloxy)-2-methyl-3-(2-methyl-5-propynoyl-phenyl)-3H-pyrimidin-4-one of Step C (10 mg, 0.02 mmol) in acetonitrile (1 mL) was added 2-hydroxy-2-methylpropionamidine HCl (5 mg, 0.03 mmol) and potassium carbonate (10 mg, 0.08 mmol) and the slurry was heated at 75° C. for eighteen hours. After cooling to room temperature the reaction was filtered to remove excess salts. The filtrate was concentrated and purified via normal phase chromatography (ethyl acetate/heptane) to provide the title compound as a yellow oil (2.9 mg, 24% yield). MS (M+H): 495

Workup

temperatureAfter cooling to room temperature the reaction
filtrationwas filtered
customto remove excess salts
concentrationThe filtrate was concentrated
custompurified via normal phase chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record: ord-414ed8fd65af410d9e1a24852356e9a8
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056110B2

Reaction notes

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