Methylamine → HCID 19012209, compound

HRID 1029573Notes

Reaction equation

HRID 1029573 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7]([CH2:11][CH2:12][CH3:13])=[N:8]2)=[C:4]([CH3:14])[N:3]=1.[CH3:15][NH2:16]>C(O)C>[CH3:14][C:4]1[N:3]=[C:2]([NH:16][CH3:15])[N:10]=[C:9]2[C:5]=1[NH:6][C:7]([CH2:11][CH2:12][CH3:13])=[N:8]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 190122122-Chloro-6-methyl-8-propylpurine

Product 1

HCID 19012209HCID 19012209, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-Chloro-6-methyl-8-propylpurine (from Step 1 of Example 32) (0.1 g, 0.47 mmol) in ethanol (2 ml) was added condensed methylamine (1 ml) at -20° C. The mixture was then placed in a steel-bomb and heated at 110° C. for 7 hours. The reaction was cooled and the mixture was concentrated in vacuo. The residue was partitioned between CHCl3 and water, and the organic layer was separated and dried over MgSO4. The crude product obtained after removal of the solvent was purified by flash-chromatography on silica-gel using 5% MeOH in CHCl3 giving the titled compound as an amorphous solid (0.115 g, quantitative). NMR (CDCl3): δ1.03 (t, J=8Hz,3H), 1.8 (q, J=8 Hz, 2H), 2.64 (s, 3H), 2.8 (t, J=8 Hz, 2H), 3.0 (d, J=5 Hz, 3H), 5.1 (br s, 1H). FAB-MS: m/e 206 (M+H).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was partitioned between CHCl3 and water
  4. customthe organic layer was separated
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-e0df4a0c2ce24f7787ad7c491681607b
Source dataset
uspto-grants-1992_04
Patent number
US05102880

Reaction notes

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