Potassium Carbonate → 5-chloro-3-{5-[2-(1-hydroxy-1-methyl-ethyl)-pyrimidin-4-yl]-2-methyl-phenyl}-6-(4-methoxy-benzyloxy)-2-methyl-3H-pyrimidin-4-one

HRID 2172588Notes

Reaction equation

[Cl:1][C:2]1[C:3](=[O:30])[N:4]([C:19]2[CH:24]=[C:23]([C:25](=O)[C:26]#[CH:27])[CH:22]=[CH:21][C:20]=2[CH3:29])[C:5]([CH3:18])=[N:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.Cl.[OH:32][C:33]([CH3:38])([CH3:37])[C:34]([NH2:36])=[NH:35].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[C:3](=[O:30])[N:4]([C:19]2[CH:24]=[C:23]([C:25]3[CH:26]=[CH:27][N:36]=[C:34]([C:33]([OH:32])([CH3:38])[CH3:37])[N:35]=3)[CH:22]=[CH:21][C:20]=2[CH3:29])[C:5]([CH3:18])=[N:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 5-chloro-6-(4-methoxy-benzyloxy)-2-methyl-3-(2-methyl-5-propynoyl-phenyl)-3H-pyrimidin-4-one from Step H (660 mg, 1.56 mmol) in acetonitrile (3 mL) was added 2-hydroxy-2-methylpropionamidine HCl (324 mg, 2.34 mmol) and potassium carbonate (645 mg, 4.68 mmol) and heated at 75° C. for eighteen hours. The reaction was returned to ambient temperature and filtered to remove excess salts. The filtrate was concentrated to provide a dark red oil. Normal phase chromatography (ethyl acetate/heptanes) provided the pyrimidine as a yellow oil (336 mg, 42%). MS (M+H): 507

Workup

customwas returned to ambient temperature
filtrationfiltered
customto remove excess salts
concentrationThe filtrate was concentrated
customto provide a dark red oil

Sources & evidence

ORD record: ord-c6ea3e7725a643ce863991d3c5e9e0e0
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056110B2

Reaction notes

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