1-Naphthalenemethanamine → 2-Chloro-N-(1-naphthylmethyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine

HRID 897094Notes

Reaction equation

HRID 897094 reaction equation
[C:1]1([CH2:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:16](Cl)[N:15]=1.C(N(CC)CC)C>C(#N)C>[Cl:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:16]([NH:12][CH2:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[N:15]=1

Participants

5

Reactant 3

HCID 83551-NaphthalenemethanamineHCID 8471TriethylamineHCID 2702652,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Product 1

HCID 208168032-Chloro-N-(1-naphthylmethyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amineYield 97.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Naphthylmethanamine (5.4 g, 19.7 mmol) was added to a stirred solution of 2,6-dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (3.5 g, 22.3 mmol) (Preparation 19) and triethylamine (4 g, 39.6 mmol) in acetonitrile (150 ml) at room temperature. The reaction mixture was stirred at room temperature for 64 hours. The solvent was removed under reduced pressure, ethyl acetate (100 ml) was added and then the solvent was removed under reduced pressure again. The residue was purified by column chromatography on silica gel eluting with pentane:ethyl acetate (1:1 by volume) increasing in polarity to neat ethyl acetate. The solvent was removed under reduced pressure to give the title compound (7.56 g) as a solid.

Workup

  1. customThe solvent was removed under reduced pressure, ethyl acetate (100 ml)
  2. additionwas added
  3. customthe solvent was removed under reduced pressure again
  4. customThe residue was purified by column chromatography on silica gel eluting with pentane:ethyl acetate (1:1 by volume)
  5. temperatureincreasing in polarity to neat ethyl acetate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0b2f49b843be4b63a917353fd6358122
Source dataset
uspto-grants-2005_07
Patent number
US06921753B2

Reaction notes

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