Potassium Carbonate → HCID 59830301, compound

HRID 2060687Notes

Reaction equation

HRID 2060687 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.[NH2:32][C:33]1[C:34]([F:41])=[CH:35][C:36]([CH3:40])=[C:37]([OH:39])[CH:38]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:41][C:34]1[CH:35]=[C:36]([CH3:40])[C:37]([O:39][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 101540985-Amino-4-fluoro-2-methylphenolHCID 67397503HCID 67397503, compoundHCID 67397716HCID 67397716, compound

Product 1

HCID 59830301HCID 59830301, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methanesulfonyl-4-(1-methyl-1H-pyrazol-4-yl)-pyrimidine and 2-methanesulfinyl-4-(1-methyl-1H-pyrazol-4-yl)-pyrimidine from Example A16 (1 g, 4.2 mmol), 5-amino-4-fluoro-2-methylphenol (1.2 g, 8.5 mmol) and K2CO3 (1.2 g, 8.6 mmol) were combined in DMF (10 mL) using a procedure analogous to Example A10 to provide 2-fluoro-4-methyl-5-(4-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-yloxy)benzenamine (420 mg). 1H NMR (400 MHz, DMSO-d6): δ 8.42 (d, J=5.2 Hz, 1H), 8.39 (s, 1H), 8.07 (s, 1H), 7.40 (d, J=5.2 Hz, 1H), 6.90 (d, J=9.6 Hz, 1H), 6.47 (d, J=8.4 Hz, 1H), 5.02 (br s, 2H), 3.88 (s, 3H), 1.88 (s, 3H); MS (ESI) m/z: 300.2 (M+H+).

Sources & evidence

ORD record
ord-a72ef3808e744b05b6f1f5ca49af92e1
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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