Tetrahydrofuran → HCID 57663088, compound

HRID 1629632Notes

Reaction equation

HRID 1629632 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:25][CH3:26])[N:6]2[CH2:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#N)=[CH:19][CH:18]=1.[H-].[Al+3].[H-].[H-].C1C[O:34]CC1>>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:25][CH3:26])[N:6]2[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([CH:21]=[O:34])=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21584524AluminiumhydrideHCID 58019861HCID 58019861, compound

Product 1

HCID 57663088HCID 57663088, compound

Conditions

Temperature
0 °C

Procedure

4-[6-amino-8-methoxy-2-(2-methoxyethoxy)purin-9-ylmethyl]benzonitrile (100 mg) is dissolved in dry THF (3 mL) and cooled to 0° C. under argon. The aluminum hydride reagent generated above (0.72 mL) is added to the reaction flask and the mixture is stirred at 0-5° C. for 1 hour and then quenched by addition of 3 M HCl. The mixture is then extracted with ethyl acetate and then dichloromethane and concentrated in vacuo to yield 85 mg. NMR is consistent with structure assignment.

Workup

  1. additionis added to the reaction flask
  2. customquenched by addition of 3 M HCl
  3. extractionThe mixture is then extracted with ethyl acetate
  4. concentrationdichloromethane and concentrated in vacuo
  5. customto yield 85 mg

Sources & evidence

ORD record
ord-6e3d975a2f5d4c29a6a7939533109cfd
Source dataset
uspto-grants-2014_07
Patent number
US08790655B2

Reaction notes

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