Water → HCID 86655323, compound

HRID 876980Notes

Reaction equation

HRID 876980 reaction equation
[Cl:1][C:2]1[C:3]2[N:11]=[N:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]4([OH:24])[CH2:23][CH2:22][CH2:21][CH2:20]4)[N:14]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1.[CH3:25][Si:26](Cl)([CH3:28])[CH3:27].C(N(CC)CC)C.O>C1COCC1>[Cl:1][C:2]1[C:3]2[N:11]=[N:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]4([O:24][Si:26]([CH3:28])([CH3:27])[CH3:25])[CH2:23][CH2:22][CH2:21][CH2:20]4)[N:14]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6397Chlorotrimethylsilane2×HCID 8471Triethylamine2×HCID 86655324HCID 86655324, compound

Product 1

HCID 86655323HCID 86655323, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 7-chloro-3-{6-[1-hydroxy-1-cyclopentyl]pyridin-2-ylmethyl}-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ylamine (0.5 g, 1.5 mmol) in dry THF (15 mL) at room temperature was treated with trimethylsilyl chloride (0.38 mL, 3.0 mmol) then triethylamine (0.42 mL, 3.0 mmol); stirred at 35° C. overnight, treated with additional quantities of trimethylsilyl chloride (0.19 mL, 1.5 mmol) then triethylamine (0.21 mL, 1.5 mmol) and stirred at 35° C. for 24 h. The mixture was poured into water (60 mL), extracted with EtOAc (×2), concentrated in vacuo and purified by chromatography (SiO2:isohexane-EtOAc (3:1)) to give the title compound (0.55 g, 88%); NMR δH (400 MHz, DMSO) 7.78 (1H, t, J 7.8 Hz), 7.59 (2H, br s), 7.43 (1H, d, J 7.8 Hz), 7.19 (1H, d, J 7.8 Hz), 5.79 (2H, s), 1.68 (7H, m), 1.40 (2H, m), −0.11 (9H, s); (M+H)+ 418.

Workup

  1. extractionextracted with EtOAc (×2)
  2. concentrationconcentrated in vacuo
  3. custompurified by chromatography (SiO2:isohexane-EtOAc (3:1))

Sources & evidence

ORD record
ord-e74274a8183342cca6a74338ee093734
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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