Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1) → 7-Isobutyl-5-(2-morpholin-4-ylethyl)-2-(1-naphthylmethyl)-3-pyridin-4-yl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 1181685Notes

Reaction equation

Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C1CCN2C(=NCCC2)CC1.[CH2:22]([N:26]1[C:31]2=[N:32][N:33]([CH2:41][C:42]3[C:51]4[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=4)[CH:45]=[CH:44][CH:43]=3)[C:34]([C:35]3[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=3)=[C:30]2[C:29](=[O:52])[NH:28][C:27]1=[O:53])[CH:23]([CH3:25])[CH3:24]>CN(C)C=O>[CH2:22]([N:26]1[C:31]2=[N:32][N:33]([CH2:41][C:42]3[C:51]4[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=4)[CH:45]=[CH:44][CH:43]=3)[C:34]([C:35]3[CH:36]=[CH:37][N:38]=[CH:39][CH:40]=3)=[C:30]2[C:29](=[O:52])[N:28]([CH2:3][CH2:4][N:5]2[CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[C:27]1=[O:53])[CH:23]([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

4-(2-chloroethyl)morpholine hydrochloride (0.0435 g) followed by DBU (0.094 g) were added to a solution of 7-isobutyl-2-(1-naphthylmethyl)-3-pyridin-4-yl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (0.0668 g) in dimethylformamide (1 ml). The mixture was heated at 80° C. for 18 hours then cooled to room temperature. The crude reaction was purified on preparative HPLC to give the title compound (0.077 g). Mass: 538.90 (M+H).

Workup

temperaturethen cooled to room temperature
customThe crude reaction
customwas purified on preparative HPLC

Sources & evidence

ORD record: ord-f253712b955c4370ae2ee2831182f521
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285558B2

Reaction notes

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