Tetrahydrofuran → HCID 57663088, compound

HRID 2170069Notes

Reaction equation

HRID 2170069 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-ae29bd2df5c349038b20ad1d8f186f24
Source dataset
uspto-grants-2015_06
Patent number
US09050376B2

Reaction notes

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