Isoamylamine → 6-amino-2-[(3-methylbutyl)amino]-9-(tetrahydro-2H-pyran-4-ylmethyl)-7,9-dihydro-8H-purin-8-one

HRID 1011168Notes

Reaction equation

HRID 1011168 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([O:18]C)[N:8]2[CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:4]([NH2:20])[N:3]=1.[CH3:21][CH:22]([CH3:26])[CH2:23][CH2:24][NH2:25]>>[NH2:20][C:4]1[N:3]=[C:2]([NH:25][CH2:24][CH2:23][CH:22]([CH3:26])[CH3:21])[N:10]=[C:9]2[C:5]=1[NH:6][C:7](=[O:18])[N:8]2[CH2:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 7894IsoamylamineHCID 576997442-Chloro-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-Purin-6-amine

Product 1

HCID 250255576-amino-2-[(3-methylbutyl)amino]-9-(tetrahydro-2H-pyran-4-ylmethyl)-7,9-dihydro-8H-purin-8-one

Conditions

Temperature
170 °C

Procedure

A mixture of 2-chloro-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (45 mg) in 3-methyl-1-butylamine (0.234 mL) was heated in a microwave at 170° C. for 10 mins. The mixture was concentrated in vacuo to give a green oily residue. This was purified by C18 reverse phase chromatography (ISCO) using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluent (20-60%) to give the title compound as a white solid (10 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a green oily residue
  3. customThis was purified by C18 reverse phase chromatography (ISCO)

Sources & evidence

ORD record
ord-5cd821706a45411ab98e52c90041014d
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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