Diisopropylethylamine → N-(2-(benzyloxy)-5-nitrophenyl)-2-chloro-5-fluoropyrimidin-4-amine

HRID 1482688Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:10]=1[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[N:25]=[C:24](Cl)[C:23]([F:27])=[CH:22][N:21]=1.CCN(C(C)C)C(C)C.C(Cl)Cl.CCCCCC.C(OCC)(=O)C>C(O)CCC.O>[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:10]=1[NH:11][C:22]1[C:23]([F:27])=[CH:24][N:25]=[C:20]([Cl:19])[N:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

In a pressure tube 2-(benzyloxy)-5-nitroaniline (0.65 g), 2,4-dichloro-5-fluoropyrimidine (0.66 g) and DIPEA (0.69 g) were taken in n-butanol (10 mL). The reaction mixture was heated at 120° C. for 24 hr. The reaction was monitored on TLC using DCM:hexane:ethyl acetate (3:5:2) as mobile phase. The reaction was complete after 24 h. After completion, reaction mixture was allowed to cool at room temperature. The reaction was poured into water and extracted with ethyl acetate (3×25 mL). The ethyl acetate layer washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure at 40° C. Crude material was purified by triturating with diethyl ether to give 0.25 g of N-(2-(benzyloxy)-5-nitrophenyl)-2-chloro-5-fluoropyrimidin-4-amine. M+1=374.8.

Workup

customAfter completion, reaction mixture
temperatureto cool at room temperature
extractionextracted with ethyl acetate (3×25 mL)
washThe ethyl acetate layer washed with brine solution
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure at 40° C
customCrude material was purified
customby triturating with diethyl ether

Sources & evidence

ORD record: ord-6fdbeb31999a41918e8b0fc24bf2f550
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09415049B2

Reaction notes

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