Diisopropylethylamine → HCID 57540720, compound

HRID 906230Notes

Reaction equation

HRID 906230 reaction equation
O[C:2]1[C:3](=[O:17])[N:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[F:60][C:61]([F:71])([F:70])[O:62][C:63]1[CH:68]=[CH:67][C:66]([SH:69])=[CH:65][CH:64]=1>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:4]2[CH:5]=[CH:6][N:7]=[C:2]([S:69][C:66]3[CH:65]=[CH:64][C:63]([O:62][C:61]([F:60])([F:70])[F:71])=[CH:68][CH:67]=3)[C:3]2=[O:17])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 27773604-(Trifluoromethoxy)thiophenolHCID 178490807HCID 178490807, compound

Product 1

HCID 57540720HCID 57540720, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 3-hydroxy-1-(4-methoxybenzyl)pyrazin-2(1H)-one (2.0 g, 8.61 mmol), PyBOP (7.84 g, 15.07 mmol) and N,N-diisopropylethylamine (4.51 mL, 8 mmol) in DMF (40 mL) was stirred at RT under N2 for 3 hours whereupon 4-(trifluoromethoxy)benzenethiol (2.007 g, 10.33 mmol) was added. After having stirred for 18 additional hours, the reaction was diluted with saturated aq. NaHCO3 (65 ml) and was then extracted with EtOAc (60 ml). The EtOAc layer was dried over Na2SO4 and concentrated. The crude product was purified by silica gel chromatography employing a solvent gradient (hexane to 75% EtOAc/hexane) to elute 1-(4-methoxybenzyl)-3-(4-(trifluoromethoxy)phenylthio)pyrazin-2(1H)-one (2.76 g, 6.42 mmol, 74.6% yield) as white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 7.58 (2H, d, J=8.78 Hz), 7.21-7.35 (4H, m), 7.02 (1H, d, J=4.52 Hz), 6.90 (2H, d, J=8.78 Hz), 6.85 (1H, d, J=4.27 Hz), 5.03 (2H, s), 3.81 (3H, s).

Workup

  1. additionwas added
  2. extractionwas then extracted with EtOAc (60 ml)
  3. dry with materialThe EtOAc layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4490cdc9060249108e915b08c87930bb
Source dataset
uspto-grants-2011_09
Patent number
US08012984B2

Reaction notes

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