(R)-8-cyclopentyl-7-ethyl-5-methyl-2-(2-oxo-2-phenylethyl)-7,8-dihydropteridin-6(5H)-one → (R,Z)-8-cyclopentyl-2-(1-(dimethylamino)-3-oxo-3-phenylprop-1-en-2-yl)-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

HRID 44869Notes

Reaction equation

[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([CH2:16][C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:25])[C:8](=[O:26])[C@H:7]2[CH2:27][CH3:28])[CH2:5][CH2:4][CH2:3][CH2:2]1>CN(C(OC)OC)C>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13](/[C:16](/[C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:1]/[N:6]([CH3:15])[CH3:7])[N:12]=[CH:11][C:10]=3[N:9]([CH3:25])[C:8](=[O:26])[C@H:7]2[CH2:27][CH3:28])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of (R)-8-cyclopentyl-7-ethyl-5-methyl-2-(2-oxo-2-phenylethyl)-7,8-dihydropteridin-6(5H)-one (Intermediate B-1, 700 mg) in 10 mL of DMF-DMA was heated at 110° C. for 3 hours. The resulting mixture was concentrated to give the desired (R,Z)-8-cyclopentyl-2-(1-(dimethylamino)-3-oxo-3-phenylprop-1-en-2-yl)-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (compound I-132).

Workup

concentrationThe resulting mixture was concentrated

Sources & evidence

ORD record: ord-ccdd0958a18a4516abb7508bdf689562
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541418B2

Reaction notes

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