Methyl iodide → 6-chloro-9-methyl-9H-purin-2-amine

HRID 1007156Notes

Reaction equation

HRID 1007156 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[H-].[Na+].I[CH3:15]>CN(C=O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:15])=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53603492-Amino-6-chloropurine

Product 1

HCID 108213316-chloro-9-methyl-9H-purin-2-amineYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2-amino-6-chloropurine (1.08 g, 6.4 mmol) was suspended in dry DMF (75 ml) and treated with sodium hydride, 60% dispersion (0.28 g, 7 mmol). The suspension was stirred for 15 min before iodomethane (0.44 ml, 7.06 mmol) was added and the resulting yellow solution stirred for 1 hr 45 min. The solid was filtered and the filtrate evaporated before addition of water for 10 min. The resulting solid was filtered and dried overnight to give the product as a mixture of N-7 and N-9 alkylation products. The residual liquor was left overnight and more crystals were collected the next day and dried. Yield=77%.

Workup

  1. additionwas added
  2. filtrationThe solid was filtered
  3. customthe filtrate evaporated before addition of water for 10 min
  4. filtrationThe resulting solid was filtered
  5. customdried overnight
  6. customto give the product
  7. additionas a mixture of N-7 and N-9 alkylation products
  8. waitThe residual liquor was left overnight
  9. custommore crystals were collected the next day
  10. customdried

Sources & evidence

ORD record
ord-d3b8f6a8b7a54eb0b86997e6c87865b4
Source dataset
uspto-grants-2004_09
Patent number
US06794390B2

Reaction notes

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