4-Nitrophenol → 4-Methylsulfanyl-6-(4-nitro-phenoxy)-pyrimidine

HRID 659026Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Cl[C:14]1[CH:19]=[C:18]([S:20][CH3:21])[N:17]=[CH:16][N:15]=1>CN(C=O)C.C(OCC)(=O)C.O>[CH3:21][S:20][C:18]1[CH:19]=[C:14]([O:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:15]=[CH:16][N:17]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 4-nitrophenol (8.04 g, 58 mmol) in DMF (36 ml) is added at 0° C. sodium hydride (2.5 g, 63 mmol, 60% in mineral oil) and stirring is continued for 30 minutes at r.t. A solution of 4-chloro-6-methylsulfanyl-pyrimidine (8.44 g, 52.5 mmol) in DMF (12 ml) is added and the reaction mixture is sealed in a reaction tube and heated in the microwave to 130° C. for 20 minutes. The reaction mixture is taken up in ethyl acetate and water. The organic phase is washed dried and evaporated. Recrystallization from ethyl acetate results in 6.08 g (44%) of an off-white powder of sufficient purity.

Workup

customthe reaction mixture is sealed in a reaction tube
washThe organic phase is washed
customdried
customevaporated
customRecrystallization from ethyl acetate

Sources & evidence

ORD record: ord-c9cbaa9f222a409eae70942ff65d28ef
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080552B2

Reaction notes

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