Ammonia → 4-Chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidine

HRID 2189043Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16](=O)[NH:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:5][CH:4]=1)[CH3:2].P(Cl)(Cl)([Cl:27])=O.N>O>[Cl:27][C:16]1[C:17]2[C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][CH:7]=3)=[C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:11][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Put 72 g (227.6 mmol) 5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4(3H)-one in 360 ml (4.6 mol) phosphoryl chloride and heat to reflux. Stir the mixture for approx. 1 h at 120° C., before adding the reaction mixture dropwise, after cooling to RT, at controlled dose and with vigorous stirring, to a mixture of 2.2 liters of 25% ammonia solution and 1.2 liters water (pH>9, temperature 55-75° C.). Extract the aqueous mixture three times with dichloromethane, combine the organic phases, dry over sodium sulphate and concentrate by vacuum evaporation. Wash the residue with a little diisopropyl ether, and after filtration and drying at high vacuum, 66.1 g (85.2% of theor.) of the target product is obtained.

Workup

additionbefore adding the reaction mixture dropwise
extractionExtract the aqueous mixture three times with dichloromethane
dry with materialdry over sodium sulphate
concentrationconcentrate by vacuum evaporation
washWash the residue with a little diisopropyl ether
filtrationafter filtration
customdrying at high vacuum, 66.1 g (85.2% of theor.) of the target product
customis obtained

Sources & evidence

ORD record: ord-e0107dde97474b6896d605e1f63656ee
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324222B2

Reaction notes

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