Water → HCID 67193541, compound

HRID 2401320Notes

Reaction equation

[CH:1]1([C:6]2[NH:14][C:13]3[C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH3:18])[C:10](Cl)=[N:9][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH3:21][O:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH2:31])=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C.O>CN1CCCC1=O>[CH3:21][O:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH:31][C:10]2[N:11]([CH2:16][CH2:17][CH3:18])[C:12](=[O:15])[C:13]3[NH:14][C:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)=[N:7][C:8]=3[N:9]=2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 8-cyclopentyl-2-chloro-1-propyl-1,7-dihydro-purin-6-one (0.15 g, 0.535 mmol) in N-methyl-pyrrolidone (1 ml) was added methyl-4-(amino methyl)benzoate hydrochloride (0.216 g, 1.07 mmol) followed by diisopropylethylamine (242 mg, 1.874 mmol) and the resulting reaction mixture was heated at 150° C. overnight. To the reaction mixture was added water and the product was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulphate and concentrated under vacuum. The crude product was purified by preparative TLC using 5% methanol in dichloromethane as solvent system to give the product (0.11 g, 50%) as an off white solid.

Workup

customthe resulting reaction mixture
extractionthe product was extracted with ethyl acetate
dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulphate
concentrationconcentrated under vacuum
customThe crude product was purified by preparative TLC

Sources & evidence

ORD record: ord-358722c001a142bfaab57c873f283d81
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796290B2

Reaction notes

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