Potassium Carbonate → HCID 58318876, compound

HRID 2401496Notes

Reaction equation

HRID 2401496 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#[N:6].[OH:11][C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([O:11][C:12]2[CH:13]=[N:14][CH:15]=[N:16][CH:17]=2)[CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 565855Pyrimidin-5-olHCID 5872043,5-Difluorobenzonitrile

Product 1

HCID 58318876HCID 58318876, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,5-Difluorobenzonitrile (1.0 g, 7.2 mmol, 1.0 eq), 5-hydroxypyrimidine (691 mg, 7.19 mmol, 1.00 eq), K2CO3 (1.2 g, 8.7 mmol, 1.2 eq) and DMF (17 mL) were added to a microwave vial and microwaved at 150° C. for 15 minutes. The reaction was filtered and concentrated on silica gel (5 g). The silica gel was loaded on top a fresh bed of silica gel and washed with 50% ethyl acetate/hexane. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 750 mg (48%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 9.08 (s, 1H), 8.75 (s, 2H), 7.71 (ddd, J=8.4, 2.2, 1.2 Hz, 1H), 7.62-7.61 (m, 1H), 7.56 (dt, J=10.0, 2.3 Hz, 1H); [M+1]+: 216.1.

Workup

  1. custommicrowaved at 150° C. for 15 minutes
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated on silica gel (5 g)
  4. washwashed with 50% ethyl acetate/hexane
  5. customThe solvents were removed in vacuo
  6. customthe crude mixture was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f351e082815047f1b63a98d0e871386e
Source dataset
uspto-grants-2014_08
Patent number
US08796295B2

Reaction notes

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