Potassium Carbonate → HCID 67958114, compound

HRID 527673Notes

Reaction equation

HRID 527673 reaction equation
[CH3:1][CH:2]1[C:11]2[C:10]([OH:12])=[CH:9][CH:8]=[CH:7][C:6]=2[O:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].Cl[C:20]1[N:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][N:21]=1>CN(C=O)C>[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][C:20]2[N:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][N:21]=2)[O:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 825442-Chloro-5-nitropyrimidineHCID 67958147HCID 67958147, compound2×

Product 1

HCID 67958114HCID 67958114, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-methyl-3,4-dihydro-2Hchromen-5-ol (Intermediate 211, 111 mg, 0.676 mmol) was dissolved in 5.0 mL of DMF. K2CO3 (140 mg, 1.01 mmol) and 2-chloro-5-nitropyrimidine (162 mg, 1.01 mmol) were added and the reaction mixture was stirred for 1 hour at room temperature. DMF was then evaporated under high vacuum and the residue was purified by flash chromatography on silica gel using cyclohexane/ethyl acetate from 1:0 to 7:3 as eluents affording the title compound (192 mg).

Workup

  1. customDMF was then evaporated under high vacuum
  2. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-8761646469004ece8e64c7a419f33e44
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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