Cesium carbonate → HCID 67406094, compound

HRID 1774425Notes

Reaction equation

Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:4][N:3]=1.[OH:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.O.ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[OH:20][C:21]1[CH:26]=[C:25]([C:2]2[N:7]([CH3:8])[C:6](=[O:9])[C:5]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:4][N:3]=2)[CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 2 g (7.12 mmol) 2-chloro-5-[(4-methoxybenzyl)oxy]-3-methylpyrimidin-4(3H)-one in 20 ml THF was added 521 mg (0.712 mmol) 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane adduct, 1.33 g (9.62 mmol) 3-hydroxyphenylboronic acid, and 11.4 ml (11.4 mmol) 1 M aq Cs2CO3. The reaction mixture was heated to 120° C. for 30 min in the microwave, then diluted with 10 ml water, extracted with 100 ml EtOAc, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography (50 g silica gel, 0-100% EtOAc:hexane) gave 340 mg (14% yield) of 2-(3-hydroxyphenyl)-5-[(4-methoxybenzyl)oxy]-3-methylpyrimidin-4(3H)-one. LCMS [M+H]+=339.0.

Workup

extractionextracted with 100 ml EtOAc
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by flash chromatography (50 g silica gel, 0-100% EtOAc:hexane)

Sources & evidence

ORD record: ord-d2ecd7a35fc54df4a81a6ab75f49bd8d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260413B2

Reaction notes

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