Sodium Carbonate → HCID 131735904, compound

HRID 2207393Notes

Reaction equation

HRID 2207393 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[N:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=2)[CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].Br[C:35]1[CH:36]=[N:37][CH:38]=[C:39]([F:41])[CH:40]=1>CC1CCCO1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[F:41][C:39]1[CH:40]=[C:35]([C:6]2[CH:5]=[C:4]([NH:17][C:18]3[N:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=[CH:20][N:19]=3)[CH:3]=[C:2]([CH3:1])[CH:7]=2)[CH:36]=[N:37][CH:38]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 8202063-Bromo-5-fluoropyridineHCID 58456089N-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine

Product 1

HCID 131735904HCID 131735904, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 73012-MethyltetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (1.00 g, 2.64 mmol), Na2CO3 (2.64 mL, 5.27 mmol, 2.0 M), and 3-bromo-5-fluoropyridine (0.511 g, 2.90 mmol) in 2-methyl tetrahydrofuran (13.0 mL) was purged with argon (3×), then Pd(dppf)Cl2—CH2Cl2 (0.108 g, 0.132 mmol) was added. The reaction was purged with argon (3×) and heated to 80° C. The reaction was monitored by LC/MS and upon completion was cooled to ambient temperature. The reaction mixture was filtered through a CELITE plug and washed with dichloromethane. The eluent was diluted with water and the organic layer was extracted, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography (acetone/hexanes) to afford N-[3-(5-fluoropyridin-3-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine. MS APCI calc'd for C17H19F4N4 [M+H]+ 349. found 349.

Workup

  1. customwas purged with argon (3×)
  2. customThe reaction was purged with argon (3×)
  3. temperaturewas cooled to ambient temperature
  4. filtrationThe reaction mixture was filtered through a CELITE plug
  5. washwashed with dichloromethane
  6. additionThe eluent was diluted with water
  7. extractionthe organic layer was extracted
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography (acetone/hexanes)

Sources & evidence

ORD record
ord-d30b530cd6994af09b89c714f4a7affb
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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