Cesium carbonate → HCID 90314324, compound

HRID 1524036Notes

Reaction equation

HRID 1524036 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:15]([OH:24])=[CH:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=3)=[CH:10][C:9]=2[F:25])=[N:6][CH:7]=1.Cl[C:27]1[CH:32]=[CH:31][N:30]=[C:29]([NH2:33])[N:28]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][C:15]=3[O:24][C:27]3[CH:32]=[CH:31][N:30]=[C:29]([NH2:33])[N:28]=3)=[CH:10][C:9]=2[F:25])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2233322-Amino-4-chloropyrimidineHCID 136499144HCID 136499144, compound

Product 1

HCID 90314324HCID 90314324, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a 5 mL vial were added a stir bar, 4′-(5-aminopyrazin-2-yl)-3′-fluoro-4-(trifluoromethyl)biphenyl-2-ol (40 mg, 0.12 mmol), 4-chloropyrimidin-2-amine (17.8 mg, 0.14 mmol), DMSO (1 mL) and Cs2CO3 (52 mg, 0.16 mmol). The vial was flushed with nitrogen and heated for 15 hours at 120° Celsius. The reaction was diluted with 5 mL of ethyl acetate and 5 mL of brine. The aqueous layer was then extracted with ethyl acetate (3×10 mL), the combined organic extracts dried over Na2SO4, and concentrated to dryness. The crude product was purified by HPLC to give the title compound. MS (ESI): mass calcd. for C21H14F4N6O, 442.12; m/z found, 443.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.34 (s, 1H), 8.09-8.07 (d, J=1.4, 1H), 8.07-8.05 (d, J=7.0, 1H), 7.96-7.88 (m, 1H), 7.82-7.74 (d, J=1.6, 2H), 7.71 (s, 1H), 7.41-7.37 (dd, J=8.1, 1.7, 1H), 7.37-7.32 (dd, J=12.4, 1.7, 1H), 6.64-6.56 (d, J=7.0, 1H).

Workup

  1. additionTo a 5 mL vial were added a stir bar
  2. customThe vial was flushed with nitrogen
  3. additionThe reaction was diluted with 5 mL of ethyl acetate and 5 mL of brine
  4. extractionThe aqueous layer was then extracted with ethyl acetate (3×10 mL)
  5. dry with materialthe combined organic extracts dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-d5a55cf6311542e4932d074bbf5849de
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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