Water → (2-Chloro-9-cyclopentyl-9H-purin-6-yl)-(3,4-dimethoxy-benzyl)-amine

HRID 1432377Notes

Reaction equation

HRID 1432377 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[N:3]=1.[H-].[Na+].[CH:25]1(Br)[CH2:29][CH2:28][CH2:27][CH2:26]1.O>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:4]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 178490985HCID 178490985, compound

Product 1

HCID 18002120(2-Chloro-9-cyclopentyl-9H-purin-6-yl)-(3,4-dimethoxy-benzyl)-amineYield 46.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2-Chloro-9H-purin-6-yl)-(3,4-dimethoxy-benzyl)-amine (799 mg, 2.5 mmol) was dissolved in dry DMF (10 mL). NaH (78 mg, 3.25 mmol) was added in portions and the resulting mixture was stirred for 1 h. Cyclopentyl bromide (633 mg, 4.25 mmol) was then added and the reaction was stirred overnight at 80° C. under N2. After cooling, H2O (50 mL) was added and the mixture was extracted with CH2Cl2 (3×25 mL). The combined extracts were washed with brine (2×25 mL), dried over MgSO4, and evaporated. The residue was purified by flash chromatography (95:5 CH2Cl2/Et2O) to afford the title compound as a white powder (451 mg, 46.5%). TLC (95:5 CH2Cl2/Et2O): RF=0.27.

Workup

  1. stirringthe reaction was stirred overnight at 80° C. under N2
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with CH2Cl2 (3×25 mL)
  4. washThe combined extracts were washed with brine (2×25 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography (95:5 CH2Cl2/Et2O)

Sources & evidence

ORD record
ord-dd76bfadc0db49f6bab37dfc9c5dbaad
Source dataset
uspto-grants-2009_11
Patent number
US07612079B2

Reaction notes

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