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

HRID 1899602Notes

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.

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-72381b893646429587eda2df41eda757
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571942

Reaction notes

Loading…