Potassium Carbonate → HCID 67958162, compound

HRID 2278324Notes

Reaction equation

[CH3:1][C:2]1([CH3:13])[C:6]2=[C:7]([OH:12])[CH:8]=[CH:9][C:10]([CH3:11])=[C:5]2[O:4][CH2:3]1.Cl[C:15]1[N:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.O.C(OCC)(=O)C>[N+:21]([C:18]1[CH:17]=[N:16][C:15]([O:12][C:7]2[C:6]3[C:2]([CH3:13])([CH3:1])[CH2:3][O:4][C:5]=3[C:10]([CH3:11])=[CH:9][CH:8]=2)=[N:20][CH:19]=1)([O-:23])=[O:22]

Participants

Conditions

Temperature: 40 °C

Procedure

3,3,7-Trimethyl-2,3-dihydro-1-benzofuran-4-ol (Intermediate 27, 178 mg, 1.0 mmol) and 2-chloro-5-nitropyrimidine (191.5 mg, 1.2 mmol) were dissolved in CH3CN (3.0 mL) and K2CO3 (345.5 mg, 2.5 mmol) was added. The resulting suspension was heated to 40° C. and stirred for 1 hour. The reaction mixture was then diluted with water (50 mL) and ethyl acetate (50 mL), The organic phase was collected, washed with brine (50 mL) and dried over Na2SO4. The residue was purified by flash chromatography on silica gel using cyclohexane/ethyl acetate 97:3 as eluents affording the title compound (243 mg).

Workup

customThe organic phase was collected
washwashed with brine (50 mL)
dry with materialdried over Na2SO4
customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-6d0a6acef56644cdb7a61b6e76297d42
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133175B2

Reaction notes

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