Ethyl Acetate → HCID 67194729, compound

HRID 2401322Notes

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.[CH2:20]([O:22][C:23](=[O:26])[CH2:24][NH2:25])[CH3:21].C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>CN1CCCC1=O.O>[CH2:20]([O:22][C:23](=[O:26])[CH2:24][NH:25][C:10]1[N:11]([CH2:16][CH2:17][CH3:18])[C:12](=[O:15])[C:13]2[NH:14][C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:7][C:8]=2[N:9]=1)[CH3:21]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 8-cyclopentyl-2-chloro-1-propyl-1,7-dihydro-purin-6-one (0.10 g, 0.357 mmol) in N-methylpyrrolidone (2 ml) was added glycine ethyl ester (0.074 g, 0.532 mmol) followed by diisopropyl ethylamine (0.18 ml, 1.07 mmol). The resulting reaction mixture was heated at 130° C. overnight. To the reaction mixture was added ethyl acetate followed by water. The layers were separated. The ethyl acetate layer was washed thrice with water. The organic 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 the solvent system to give the product (0.060 g, 48%) as an off white solid.

Workup

customThe resulting reaction mixture
customThe layers were separated
washThe ethyl acetate layer was washed thrice with water
dry with materialThe organic layer was dried over anhydrous sodium sulphate
concentrationconcentrated under vacuum
customThe crude product was purified by preparative TLC

Sources & evidence

ORD record: ord-5a79a03cdb0d496e8470090f65536137
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796290B2

Reaction notes

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