Potassium Carbonate → HCID 59322792, compound

HRID 2060705Notes

Reaction equation

HRID 2060705 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.CS(C1N=C(C2C=NN(C)C=2)C=CN=1)=[O:19].[NH2:32][C:33]1[CH:38]=[CH:37][C:36](O)=[CH:35][C:34]=1[F:40].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:40][C:34]1[CH:35]=[CH:36][C:37]([O:19][C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[CH:8]=[CH:7][N:6]=2)=[CH:38][C:33]=1[NH2:32]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 27359194-Amino-3-fluorophenolHCID 67397503HCID 67397503, compoundHCID 67397716HCID 67397716, compound

Product 1

HCID 59322792HCID 59322792, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The above mixture of 2-methanesulfonyl-4-(1-methyl-1H-pyrazol-4-yl)-pyrimidine and 2-methanesulfinyl-4-(1-methyl-1H-pyrazol-4-yl)-pyrimidine (1 g, 4.2 mmol), 4-amino-3-fluoro-phenol (1.1 g, 8.6 mmol) and K2CO3 (1.2 g, 8.6 mmol) in DMF (10 mL) was heated at 100° C. for 12 h. The reaction was partitioned between H2O and EtOAc (3×50 mL). The combined organics were dried (Na2SO4), concentrated in vacuo and chromatographed to provide 2-fluoro-5-(4-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-yloxy)benzenamine (402 mg). 1H NMR (400 MHz, DMSO-d6): δ 8.44 (d, J=5.2 Hz, 1H), 8.39 (s, 1H), 8.07 (s, 1H), 7.41 (d, J=5.2 Hz, 1H), 6.98 (t, J=9.6 Hz, 1H), 6.53 (dd, J=5.6, 2.0 Hz, 1H), 6.28 (d, J=8.4 Hz, 1H), 5.25 (br s, 2H), 3.88 (s, 3H). MS (ESI) m/z: 286.2 (M+H+).

Workup

  1. customThe reaction was partitioned between H2O and EtOAc (3×50 mL)
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customchromatographed

Sources & evidence

ORD record
ord-727ec71acc3e436693b7618c796dc9d2
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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