9-Benzyl-2-chloro-9h-purin-6-amine → HCID 18332792, compound

HRID 2269106Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9](Cl)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:19][CH2:20][CH2:21][CH2:22][CH2:23][O-:24].[Na+]>C(O)CCCC>[NH2:1][C:2]1[N:10]=[C:9]([O:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 130 °C

Procedure

6-Amino-9-benzyl-2-chloropurine (150 mg, 0.58 mmol) and sodium pentylate (318 mg, 2.89 mmol) were dissolved in 1-pentanol (50 ml) and then the solution was stirred under heating at 130° C. for 5 hours. The reaction mixture was evaporated in vacuo to dryness. To the residue was added water and the mixture was extracted with chloroform. The organic layer was dried on sodium sulfate and evaporated in vacuo to dryness. The residue was purified with silica gel chromatography (2% methanol/chloroform) to give the subject compound (103 mg, yield 57%).

Workup

customThe reaction mixture was evaporated in vacuo to dryness
additionTo the residue was added water
extractionthe mixture was extracted with chloroform
customThe organic layer was dried on sodium sulfate
customevaporated in vacuo to dryness
customThe residue was purified with silica gel chromatography (2% methanol/chloroform)

Sources & evidence

ORD record: ord-56eb085edade459d9947c42f35481bf3
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329381B1

Reaction notes

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