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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 562512
Notes
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Reaction equation

HRID 562512 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-07804ed29f594eae9dc61ed710642d93
    Source dataset
    uspto-grants-2011_11
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08067417B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes