Purine → N-cyclohexyl-N-methyl-4-(1H-purin-1-ylmethyl) benzamide

HRID 343342

Reaction equation

[N:1]1[CH:9]=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.Br[CH2:11][C:12]1[CH:27]=[CH:26][C:15]([C:16]([N:18]([CH3:25])[CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:17])=[CH:14][CH:13]=1>CN(C)C(=O)C>[CH:19]1([N:18]([CH3:25])[C:16](=[O:17])[C:15]2[CH:26]=[CH:27][C:12]([CH2:11][N:1]3[CH:9]=[C:8]4[C:4](=[N:5][CH:6]=[N:7]4)[N:3]=[CH:2]3)=[CH:13][CH:14]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of purine (300 mg, 2.5 mmol) in N,N-dimethylacetamide (30 mL) was added 4-bromomethyl-N-methyl-N-cyclohexyl benzamide (852 mg, 2.75 mmol). After stirring at 80° C. for 7 hr, the reaction was stirred at room temperature for 16 hr. The solvent was removed under reduced pressure and the residue (510 mg) chromatographed (silica gel, CH2Cl2 /MeOH/90/10) to give 9 (310 mg, 35%); m.p. 229°-30° C. Anal calcd. for C20H23N5O: C, 68.71; H, 6.61; N, 20.05. Found: C, 68.24; H, 6.79; N, 19.77.

Workup

stirringthe reaction was stirred at room temperature for 16 hr
customThe solvent was removed under reduced pressure
customthe residue (510 mg) chromatographed (silica gel, CH2Cl2 /MeOH/90/10)

Sources & evidence

ORD record: ord-229242a567984e1eaab6fedc74fc9528
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05861403

Linked notes

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