2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 11374417, compound

HRID 899319Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[N:10]=[C:11]3[C:16]([OH:17])=[N:15][C:14]([CH3:18])=[N:13][C:12]=23)=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[F:36][C:37]([F:48])([F:47])[CH2:38]OS(C(F)(F)F)(=O)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[N:10]=[C:11]3[C:16](=[O:17])[N:15]([CH2:38][C:37]([F:48])([F:47])[F:36])[C:14]([CH3:18])=[N:13][C:12]=23)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 3-(4-chlorophenyl)-2-(2-chlorophenyl)-5-methyl-2H-pyrazolo[4,3-d]pyrimidin-7-ol (I-4A-1a, 1.86 g, 5.0 mmol) in anhydrous THF (30 ml) at room temperature was added lithium hexamethyidisilazide (7.5 ml, 7.5 mmol). A reddish solution was formed. Trifluoromethanesulfonic acid 2,2,2-trifluoroethyl ester (2,2 ml, 15 mmol) was subsequently added in one portion. The reaction mixture was stirred at 60° C. for 1.5 h, quenched with water, and concentrated under vacuum. MeOH was added to the residue to give a slurry which was then cooled to 0° C. A yellowish solid was formed and collected by filtration to give the desired product 4A-1 (1.63 g, 72%): MS (m/z) 453.1 (M+H)+; 1H NMR (400 MHz, CDCl3): δ 7.55-7.52 (m, 1H), 7.46-7.40 (m, 2H), 7.39-7.32 (m, 2H), 7.31-7.28 (m, 2H), 5.00-4.80 (br m, 2H), 2.87 (q, J=7.1 Hz, 2H), 1.37 (t, J=7.1 Hz, 3H).

Workup

customA reddish solution was formed
customquenched with water
concentrationconcentrated under vacuum
additionMeOH was added to the residue
customto give a slurry which
temperaturewas then cooled to 0° C
customA yellowish solid was formed
filtrationcollected by filtration

Sources & evidence

ORD record: ord-d357e9539ccd4c8393c7683ebfc307fa
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354929B2

Reaction notes

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