Ammonia → HCID 86715504, compound

HRID 2284593Notes

Reaction equation

HRID 2284593 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[C:16]([CH3:21])[CH:15]=3)=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1.[NH3:22].O1CCOCC1>O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:9]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH2:22])[N:7]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:15][C:16]=1[CH3:21]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 86715503HCID 86715503, compound

Product 1

HCID 86715504HCID 86715504, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4-(2-(4-Fluoro-3-methylphenyl)pyridin-3-yl)pyrimidin-2-amine (Compound 919) was prepared as follows: A screw capped vial was charged with 2-chloro-4-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)pyrimidine (125 mg), 28% aq. Ammonia (3 mL), 1,4-dioxane (3 mL) and a stir bar. The vial was capped tightly, heated and stirred at 60° C. for 12 h. The heterogeneous solution was cooled to room temperature, diluted with water, filtered. The solid (90 mg) was suspended in 50% EtOAc/hexanes, stirred and heated at 80° C. for 30 min. Upon cooling to room temperature, the suspension was filtered and the solid was suction dried to provide 4-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)pyrimidin-2-amine as a white solid (73 mg). 1H NMR (300 MHz, DMSO-d6): δ 8.69 (dd, J=4.7, 1.7 Hz, 1H), 8.07 (d, J=5.0 Hz, 1H), 7.93 (dd, J=7.8, 1.7 Hz, 1H), 7.47 (dd, J=7.8, 4.8 Hz, 1H), 7.38 (dd, J=7.4, 1.6 Hz, 1H), 7.18-6.95 (m, 2H), 6.70 (s, 2H), 6.20 (d, J=5.0 Hz, 1H), 2.19 (s, 3H). 19F NMR (282 MHz, DMSO-d6): δ −118.16 (q, J=7.7 Hz).LCMS: rt 4.40 min (A), purity 99%, MS (m/e) 281 MH+.

Workup

  1. custom4-(2-(4-Fluoro-3-methylphenyl)pyridin-3-yl)pyrimidin-2-amine (Compound 919) was prepared
  2. customA screw capped vial
  3. customThe vial was capped tightly
  4. temperatureheated
  5. temperatureThe heterogeneous solution was cooled to room temperature
  6. filtrationfiltered
  7. stirringstirred
  8. temperatureheated at 80° C. for 30 min
  9. temperatureUpon cooling to room temperature
  10. filtrationthe suspension was filtered
  11. customdried

Sources & evidence

ORD record
ord-4842564d727244a88431969e253a4640
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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