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

HRID 2274271Notes

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-02b2cc8e6db94f24be6f41b629d4208b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126950B2

Reaction notes

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