Water → HCID 86655323, compound

HRID 2096683Notes

Reaction equation

HRID 2096683 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

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-6561a44c17ac451080b2de59c28bbd3a
Source dataset
uspto-grants-2013_05
Patent number
US08450328B2

Reaction notes

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