Potassium Carbonate → 4-[2-[(3-fluorophenyl)amino]-4-pyridinyl]-N-(2-methoxypropyl)-2-pyrimidinamine

HRID 913299Notes

Reaction equation

HRID 913299 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=3)[CH:9]=2)[CH:5]=[CH:4][N:3]=1.Cl.[CH3:23][O:24][CH:25]([CH3:28])[CH2:26][NH2:27].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[F:21][C:17]1[CH:16]=[C:15]([NH:14][C:10]2[CH:9]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:27][CH2:26][CH:25]([O:24][CH3:23])[CH3:28])[N:7]=3)[CH:13]=[CH:12][N:11]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 171780352-Methoxypropan-1-amine hydrochlorideHCID 866467814-(2-chloro-4-pyrimidinyl)-N-(3-fluorophenyl)-2-pyridinamine2×

Product 1

HCID 673888874-[2-[(3-fluorophenyl)amino]-4-pyridinyl]-N-(2-methoxypropyl)-2-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(2-chloro-4-pyrimidinyl)-N-(3-fluorophenyl)-2-pyridinamine (i.e., the product of Step C) (55 mg, 0.18 mmol) in toluene (3.0 mL) was added 2-methoxy-1-aminopropane hydrochloride (125 mg, 1.0 mmol) and potassium carbonate (200 mg, 1.5 mmol). The mixture was stirred at 100° C. for 2 h and then allowed to cool to room temperature. The mixture was partitioned with water and ethyl acetate and the water layer was decanted. The organic layer was washed with brine and passed through a Celite® containing drying tube. The solvent was evaporated, and the resulting residue was chromatographed using 5% to 60% ethyl acetate in hexanes as eluant to give an oil which solidified upon standing. This solid was suspended in hexanes, filtered and washed with hexanes to give 25 mg of the title compound as a yellow solid, m.p. 103-105° C.

Workup

  1. temperatureto cool to room temperature
  2. customThe mixture was partitioned with water and ethyl acetate
  3. customthe water layer was decanted
  4. washThe organic layer was washed with brine
  5. additioncontaining
  6. customdrying tube
  7. customThe solvent was evaporated
  8. customthe resulting residue was chromatographed
  9. customto give an oil which
  10. filtrationfiltered
  11. washwashed with hexanes

Sources & evidence

ORD record
ord-9634d3bc90e64383a226e1c21c562f92
Source dataset
uspto-grants-2011_09
Patent number
US08026359B2

Reaction notes

Loading…