Potassium Carbonate → HCID 18327487, compound

HRID 1250192Notes

Reaction equation

HRID 1250192 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([NH:11][C:12]2[N:17]=[C:16]([S:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH:15]=[CH:14][N:13]=2)=[CH:5][C:4]=1[OH:26].[C:27](=O)([O-])[O:28]CC.[C:33](=O)([O-])[O-].[K+].[K+].CCCCCC.C(OCC)(=O)C>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]([O:26][CH3:33])=[CH:5][C:6]([NH:11][C:12]2[N:17]=[C:16]([S:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH:15]=[CH:14][N:13]=2)=[CH:7][C:8]=1[O:9][CH2:10][CH2:27][OH:28]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 18327501HCID 18327501, compoundHCID 21226206Ethyl acetate hexaneHCID 21226545CID 21226545

Product 1

HCID 18327487HCID 18327487, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[4,5-Dimethoxy-3-(2-hydroxyethoxy)phenyl]-4-(4-fluorophenylsulphanyl)-pyrimidine-2-amine was prepared by treating a solution of N-(4,5-dimethoxy-3-hydroxyphenyl)-4-(4-fluorophenylsulphanyl)-2-pyrimidineamine (2.23 g, 6.0 mmol) and ethyl carbonate (0.79 g, 9.0 mmol) in dry DMF (25 ml) with potassium carbonate (1.66 h, 12.0 mmol) and heating the resulting mixture at 100° for 16 h. The reaction was concentrated under reduced pressure and the residue partitioned between ethly acetate and water. The aqueous layer was re-extracted with ethyl acetate, the combined organic layers dried (MgSO4) and evaporated to give a residue which was subjected to column chromatography [silica; 20% hexane-ethyl acetate] to give the desired compound (1.36 g) as a white foam. δH (d6 DMSO) 9.48 (1H, s), 8.17 (1H, d, J 5.3 Hz), 7.69 (2H, m), 7.36 (2H, t, J 8.8 Hz), 7.08 (2H, m), 6.15 (1H, d, J 5.3 Hz), 4.81 (1H, t, J 5.2Hz), 3.92 (2H, t, J 5.2 Hz), 3.73 (2H, m), 3.71 (3H, s) and 3.64 (3H, s).

Workup

  1. temperatureheating the resulting mixture at 100° for 16 h
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customthe residue partitioned between ethly acetate and water
  4. extractionThe aqueous layer was re-extracted with ethyl acetate
  5. dry with materialthe combined organic layers dried (MgSO4)
  6. customevaporated
  7. customto give a residue which

Sources & evidence

ORD record
ord-092327c624174dbd95e8f5ce2031e1d2
Source dataset
uspto-grants-2002_01
Patent number
US06337335B1

Reaction notes

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