Triethylamine → 2-cyclopentyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl trifluoromethanesulfonate

HRID 1509030Notes

Reaction equation

HRID 1509030 reaction equation
[CH:1]1([C:6]2[N:7]=[C:8]([OH:16])[C:9]3[S:15][CH2:14][CH2:13][CH2:12][C:10]=3[N:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[F:24][C:25]([F:31])([F:30])[S:26](O)(=[O:28])=[O:27]>C(Cl)Cl>[F:24][C:25]([F:31])([F:30])[S:26]([O:16][C:8]1[C:9]2[S:15][CH2:14][CH2:13][CH2:12][C:10]=2[N:11]=[C:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[N:7]=1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 1785174212-cyclopentyl-1,6,7,8-tetrahydrothiopyrano[3,2-d]pyrimidin-4-one

Product 1

HCID 903386872-cyclopentyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl trifluoromethanesulfonateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-cyclopentyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-ol (2.9 g, 12.3 mmol) in methylene chloride (100 mL) at 0° C. was added N,N-dimethylaminopyridine (0.020 g, cat.), triethylamine (3.5 mL, 24.6 mmol) and trifluoromethanesulfonic acid (2.3 mL, 13.5 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 (3.40 g, 75%) as, a yellow solid. MW=368.40. 1H NMR (CDCl3, 500 MHz) δ 3.28-3.20 (m, 1H), 3.10-3.05 (m, 1H), 2.98 (t, J=6.5 Hz, 2H), 2.31-2.24 (m, 2H), 2.09-1.99 (m, 2H), 1.89-1.76 (m, 4H), 1.70-1.62 (m, 2H); APCI MS m/z 369 [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-842bcd95a150468097cf138255f7609c
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

Loading…