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Ammonium Hydroxide → (R)-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridin-7-amine

HRID 39342
Notes
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Reaction equation

HRID 39342 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]3[CH:12]=[N:13][N:14]=[C:7]3[C@@H:6]([CH2:15][CH3:16])[N:5]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:4]=2[N:3]=1.[OH-].[NH4+:23]>>[CH:17]1([N:5]2[C:4]3[N:3]=[C:2]([NH2:23])[N:11]=[CH:10][C:9]=3[N:8]3[CH:12]=[N:13][N:14]=[C:7]3[C@H:6]2[CH2:15][CH3:16])[CH2:21][CH2:20][CH2:19][CH2:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 59389586(R)-7-chloro-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridine

Product 1

HCID 24890788(R)-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridin-7-amineYield 36%

Procedure

A solution of (R)-7-chloro-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridine (500 mg, 1.64 mmol) in ammonium hydroxide (10 ml) was heated under microwave irradiation at 140° C. for 30 minutes. The solvent was removed under reduced pressure and cold water (5 mL) was added. The resulting light brown solid was filtered under vacuum and washed with cold water to give the title compound (170 mg, 36% yield).

Workup

custom
The solvent was removed under reduced pressure and cold water (5 mL)
  • additionwas added
  • filtrationThe resulting light brown solid was filtered under vacuum
  • washwashed with cold water
  • Sources & evidence

    ORD record
    ord-92a98c24ee5e48bcbb9f5aadfbcde2e3
    Source dataset
    uspto-grants-2013_09
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08524902B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes