Guanidine → 2-Di-n-propylamino-8-(2-aminopyrimidin-4-yl)-1,2,3,4-tetrahydronaphthalene

HRID 22148

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

2-Di-n-propylamino-8-(1-oxo-3-(dimethylamino)-prop-2-enyl)-1,2,3,4-tetrahydronaphthalene, prepared as in Example 8 (0.18 g; 0.55 mmol) was dissolved in 3 ml of ethanol. To the mixture was added 0.07 g (1.1 mmol) of guanidine, and the mixture was stirred at 60° C. under nitrogen for 18 hours. The mixture then was cooled to room temperature during which a crystalline solid formed. The crystals were filtered, washed with isopropyl alcohol, ether, and dried in vacuo to give 70 mg of the title compound as glistening plates. The product was recrystallized from isopropyl alcohol to obtain colorless crystals, m.p. 188°-189° C. Analysis: Theory: C, 74.04; H, 8.70; N, 17.27; Found: C, 74.30; H, 8.70; N, 17.45.

Workup

temperatureThe mixture then was cooled to room temperature during which a crystalline solid
customformed
filtrationThe crystals were filtered
washwashed with isopropyl alcohol, ether
customdried in vacuo

Sources & evidence

ORD record: ord-7dd6d28afe984fcabec32adca10aa985
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05426226

Linked notes

Loading…