2,5-Dichloro-4-(6-fluoropyridin-2-yl)pyrimidine → HCID 178511659, compound

HRID 1963853Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[N:9]=2)[C:5]([Cl:15])=[CH:4][N:3]=1.[C@H:16]1([NH2:23])[CH2:21][CH2:20][C@H:19]([NH2:22])[CH2:18][CH2:17]1>CS(C)=O>[Cl:15][C:5]1[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[N:9]=2)=[N:7][C:2]([NH:22][C@H:19]2[CH2:20][CH2:21][C@H:16]([NH2:23])[CH2:17][CH2:18]2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 2,5-dichloro-4-(6-fluoropyridin-2-yl)pyrimidine (37 mg, 0.152 mmol), DMSO (1.5 ml) and trans-cyclohexane-1,4-diamine (87 mg, 0.758 mmol)reaction mixture was stirred at about 75° C. for about 2 hours. The reaction mixture was cooled, filter and purified by prep LC, and then lyophilized to yield 39.5 mg of the title compound as a TFA salt. LCMS (m/z): 322.2 (MH+), retention time=0.59 min.

Workup

temperatureThe reaction mixture was cooled
filtrationfilter
custompurified by prep LC

Sources & evidence

ORD record: ord-fa28fef590ab4fd191574e7e81110101
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415381B2

Reaction notes

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