Water → HCID 58548159, compound

HRID 2368227Notes

Reaction equation

HRID 2368227 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([CH:12]2[CH2:16][CH2:15][O:14][CH2:13]2)[N:6]=1)=[O:4].Br[C:18]1[CH:19]=[N:20][CH:21]=[N:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C(C)=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:18]2[CH:19]=[N:20][CH:21]=[N:22][CH:23]=2)=[N:9][CH:8]=[C:7]([CH:12]2[CH2:16][CH2:15][O:14][CH2:13]2)[N:6]=1)=[O:4]

Participants

9

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 783445-BromopyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 70097075HCID 70097075, compound

Product 1

HCID 58548159HCID 58548159, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-amino-6-(tetrahydrofuran-3-yl)pyrazine-2-carboxylic acid methyl ester (300 mg, 1.34 mmol), 5-bromopyrimidine (299 mg, 1.88 mmol) and potassium carbonate (334 mg, 2.42 mmol) in xylene (15 ml) and water (51 μl, 2.82 mmol) was evacuated and vented with argon. Palladium (II) acetate (12.1 mg, 54 μmol) and xantphos (23.3 mg, 40 μmol) were added and the reaction mixture was stirred at 140° C. for 16 hr. The reaction mixture was cooled to r.t., poured into 50 ml ethyl acetate and extracted with water. The organic phase was washed with brine and the aqueous layers were back-extracted with ethyl acetate. The organic layers were dried and the solvent was evaporated. The product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as light solid (211 mg, 52%).

Workup

  1. customwas evacuated
  2. temperatureThe reaction mixture was cooled to r.t.
  3. extractionextracted with water
  4. washThe organic phase was washed with brine
  5. extractionthe aqueous layers were back-extracted with ethyl acetate
  6. customThe organic layers were dried
  7. customthe solvent was evaporated
  8. customThe product was obtained
  9. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-74df7c363dbe45a489a56e1824a8d755
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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