2,3-Dichloropyrazine → 4-(3-Chloropyrazin-2-yl)-2-methyl-6-(methylthio)pyrimidine

HRID 1621492Notes

Reaction equation

Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[N:15]=[C:14]([S:16][CH3:17])[CH:13]=[C:12]([Sn](CCCC)(CCCC)CCCC)[N:11]=1>C1(C)C=CC=CC=1.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>[Cl:8][C:7]1[C:2]([C:12]2[CH:13]=[C:14]([S:16][CH3:17])[N:15]=[C:10]([CH3:9])[N:11]=2)=[N:3][CH:4]=[CH:5][N:6]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2,3-dichloropyrazine (0.034 mL, 0.228 mmol, Aldrich, St. Louis, Mo.), 2-methyl-4-(methylthio)-6-(tributylstannyl)pyrimidine (98 mg, 0.228 mmol) and tetrakis(triphenylphosphine)palladium (26.4 mg, 0.023 mmol, Strem Chemicals, Inc., Newburyport, Mass.) in toluene (2 mL) was stirred at 110° C. for 48 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 20% EtOAc/CH2Cl2 to give 4-(3-chloropyrazin-2-yl)-2-methyl-6-(methylthio)pyrimidine (12 mg, 21% yield). 1H NMR (300 MHz, CDCl3) δ 8.63 (d, J=2.05 Hz, 1H); 8.47 (d, J=2.19 Hz, 1H); 7.44 (s, 1H); 2.77 (s, 3H); 2.56 (s, 3H). m/z (ESI, +ve ion) 253 (M+H)+.

Workup

customThe solvent was removed in vacuo
customthe residue was purified by silica gel chromatography
washeluting with 20% EtOAc/CH2Cl2

Sources & evidence

ORD record: ord-7027c32b8f314d75a8cabd88f65098d7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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