2,6-Difluorophenyl isocyanate → 1-[6-(4-Diethylamino-phenylamino)-pyrimidin-4-yl]-3-(2,6-difluoro-phenyl)-urea

HRID 1038670Notes

Reaction equation

[CH2:1]([N:3]([CH2:18][CH3:19])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[C:15]([NH2:17])[N:14]=[CH:13][N:12]=2)=[CH:6][CH:5]=1)[CH3:2].[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[N:28]=[C:29]=[O:30]>O1CCOCC1>[CH2:18]([N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH:17][C:29]([NH:28][C:22]3[C:23]([F:27])=[CH:24][CH:25]=[CH:26][C:21]=3[F:20])=[O:30])[CH:16]=2)=[CH:8][CH:9]=1)[CH3:19]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-(4-diethylamino-phenyl)-pyrimidine-4,6-diamine (257.4 mg, 1 mmol), 2,6-difluorophenyl isocyanate (170.6 mg, 1.1 mmol) in dry dioxane (4 mL) is shaken for 1.5 h at 80° C. After evaporation of the solvent in vacuo, the residue is distributed between CH2Cl2 and half-saturated K2CO3 solution. The organic layer is dried over Na2SO4, evaporated, and the residue purified by flash chromatography (CH2Cl2/CH3OH). The combined pure fractions are evaporated, the residue triturated with CH2Cl2 and the solid filtered off and dried in vacuo to afford the title compound.

Workup

customAfter evaporation of the solvent in vacuo
dry with materialThe organic layer is dried over Na2SO4
customevaporated
customthe residue purified by flash chromatography (CH2Cl2/CH3OH)
customThe combined pure fractions are evaporated
customthe residue triturated with CH2Cl2
filtrationthe solid filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-0d755ec3413f471aac8fad78cdecbe14
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552002B2

Reaction notes

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