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

HRID 22148
Notes
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Reaction equation

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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 3520GuanidineHCID 543506572-Di-n-propylamino-8-(1-oxo-3-(dimethylamino)-prop-2-enyl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 189331832-Di-n-propylamino-8-(2-aminopyrimidin-4-yl)-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. temperatureThe mixture then was cooled to room temperature during which a crystalline solid
  2. customformed
  3. filtrationThe crystals were filtered
  4. washwashed with isopropyl alcohol, ether
  5. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes