1-Butanol → 6-Amino-2-[(cyclohexylmethyl)amino]-9-(tetrahydro-2H-Pyran-4-ylmethyl)-7,9-dihydro-8H-Purin-8-one

HRID 1011184Notes

Reaction equation

HRID 1011184 reaction equation
Br[C:2]1[N:3]([CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([NH:12][CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[N:5]=2.Cl.C([OH:32])CCC>>[NH2:11][C:8]1[N:7]=[C:6]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[N:5]=[C:4]2[C:9]=1[NH:10][C:2](=[O:32])[N:3]2[CH2:20][CH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 576996278-Bromo-N2-(cyclohexylmethyl)-9-(tetrahydro-2H-Pyran-4-ylmethyl)-9H-Purine-2,6-diamine

Product 1

HCID 576997146-Amino-2-[(cyclohexylmethyl)amino]-9-(tetrahydro-2H-Pyran-4-ylmethyl)-7,9-dihydro-8H-Purin-8-one

Conditions

Temperature
100 °C

Procedure

To a solution of 8-bromo-N2-(cyclohexylmethyl)-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purine-2,6-diamine (110 mg) in dry n-butanol (1.5 ml) was added 37% grade hydrochloric acid (1.5 ml) at RT. The reaction was heated to 100° C. for six hours. The reaction was concentrated in vacuo, taken up in water (5 ml) and neutralised by the addition of 2.0M sodium hydroxide solution. The resulting white precipitate was filtered. This was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (20-60%) to afford a white solid (20 mg).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionneutralised by the addition of 2.0M sodium hydroxide solution
  3. filtrationThe resulting white precipitate was filtered
  4. customThis was purified by C18 reverse phase chromatography

Sources & evidence

ORD record
ord-ff3e7eb1553b4c76a40b7d999a2a8d6a
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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