Water → HCID 10355149, compound

HRID 646752Notes

Reaction equation

HRID 646752 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH:11][CH3:12])=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.[OH:13][CH2:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[C:3]([C:9]([NH:11][CH3:12])=[O:10])=[N:4][C:5]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:14][OH:13])[CH:20]=2)=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 151481213-Amino-6-bromo-N-methylpyrazine-2-carboxamide

Product 1

HCID 10355149HCID 10355149, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

3-Amino-6-bromo-N-methylpyrazine-2-carboxamide (2.00 g, 8.65 mmol) was dissolved in DMF followed by addition of 3-hydroxymethyl phenyl boronic acid (1.57 g, 10.32 mmol), K2CO3 (3.0 g, 21.7 mmol) and Pd(PPh3)4 (10 mol %, 1.0 g). This mixture was stirred at 90° C. under nitrogen for 12 hours. The reaction mixture was poured into water (150 mL), and extracted with ethyl acetate (3×50 mL). The organic layers were washed with brine (50 mL) then dried over anhydrous sodium sulfate. Filteration, concentration and column chromatography on silica (50% ethylacetate/hexanes) gave a solid which was dried to afforded 2.02 g (92% yield) of the title compound; 1H NMR (400 MHz, d6-DMSO): δ0 8.80 (s, 1H), 8.74 (br, 1H), 8.01(s, 2H), 7.45 (m, 4H), 5.21(t, 1H), 4.60 (d, 2H), 2.81(d, 3H); MS (EI) for C13H14N4O2: 259.38 (MH+).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe organic layers were washed with brine (50 mL)
  3. dry with materialthen dried over anhydrous sodium sulfate
  4. concentrationFilteration, concentration and column chromatography on silica (50% ethylacetate/hexanes)
  5. customgave a solid which
  6. customwas dried

Sources & evidence

ORD record
ord-15d0875757a047a1bb9d6360c9c26c12
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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