Triethylamine → 2-(3-Chlorophenyl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl trifluoromethanesulfonate

HRID 1509026Notes

Reaction equation

HRID 1509026 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([OH:17])[C:11]3[S:16][CH2:15][CH2:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[F:25][C:26]([F:32])([F:31])[S:27](O)(=[O:29])=[O:28]>C(Cl)Cl>[F:25][C:26]([F:32])([F:31])[S:27]([O:17][C:10]1[C:11]2[S:16][CH2:15][CH2:14][C:12]=2[N:13]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:9]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 1785174682-(3-chlorophenyl)-6,7-dihydro-1H-thieno[3,2-d]pyrimidin-4-one

Product 1

HCID 903385882-(3-Chlorophenyl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl trifluoromethanesulfonateYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(3-chlorophenyl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-ol (1.9 g, 7.2 mmol) in methylene chloride (50 mL) at 0° C. was added N,N-dimethylaminopyridine (0.020 g, cat.), triethylamine (2.0 mL, 14.4 mmol) and trifluoromethanesulfonic acid (1.3 mL, 7.9 mmol). The suspension was warmed to rt and stirred for 3 h. The mixture was cooled to 0° C. and the reaction was quenched with a saturated solution of NaHCO3. The organic layer was washed a saturated solution of NaHCO3 and brine. The organic layers were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (1.23 g, 44%) as a light yellow solid. MW=396.79. 1H NMR (CDCl3, 500 MHz) δ 8.35-8.32 (m, 1H), 8.24-8.20 (m, 1H), 7.48-7.38 (m, 2H), 3.59-3.49 (m, 4H); APCI MS m/z 397 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customthe reaction was quenched with a saturated solution of NaHCO3
  3. washThe organic layer was washed a saturated solution of NaHCO3 and brine
  4. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by column chromatography (silica, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-931ad7cb1b7a4ec3b65c9991c4865e03
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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