Potassium Phosphate, Tribasic → 4-(5-Methyl-2-methylsulfanyl-pyrimidin-4-yl)-10-oxa-tricyclo[5.2.1.02,6]decane-3,5-dione

HRID 41687Notes

Reaction equation

Cl[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[CH:11]12[O:20][CH:17]([CH2:18][CH2:19]1)[CH:16]1[CH:12]2[C:13](=[O:22])[CH2:14][C:15]1=[O:21].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COCCOC>[CH3:8][C:7]1[C:2]([CH:14]2[C:13](=[O:22])[CH:12]3[CH:16]([CH:17]4[O:20][CH:11]3[CH2:19][CH2:18]4)[C:15]2=[O:21])=[N:3][C:4]([S:9][CH3:10])=[N:5][CH:6]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A microwave vial is charged with 4-chloro-5-methyl-2-methylsulfanylpyrimidine (174 mg, 1 mmol), 10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione (166 mg, 1 mmol), palladium acetate (12 mg, 0.05 mmol), X-Phos (48 mg, 0.1 mmol) and potassium phosphate (424 mg, 2 mmol). 1,2-dimethoxyethane (3 ml) is added and the reaction heated to 160° C., with stirring, for 30 minutes. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 4-(5-methyl-2-methylsulfanyl-pyrimidin-4-yl)-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione (34 mg).

Workup

additionSilica gel is added to the crude
customreaction mixture
customthe solvent is evaporated under reduced pressure
customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-1a5538eae8114f16b3a16133cfb52b25
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530667B2

Reaction notes

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