1-Butanol → HCID 21559906, compound

HRID 1578370Notes

Reaction equation

HRID 1578370 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:15][NH2:16].C(N(CC)CC)C.C(O)CCC>CO.O>[NH2:8][C:7]1[C:6]([Cl:9])=[N:5][CH:4]=[N:3][C:2]=1[NH:16][CH2:15][C:14]1[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:12]([O:11][CH3:10])[CH:13]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 8471TriethylamineHCID 794345-Amino-4,6-dichloropyrimidineHCID 79832Veratrylamine

Product 1

HCID 21559906HCID 21559906, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A reaction mixture containing 1.00 g (6.09 mmols) of 4,6-dichloro-5-aminopyrimidine, 1.22 g (7.30 mmols) of 3,4-dimethoxybenzylamine, 1.02 ml (7.30 mmols) of triethylamine and 35 ml of 1-butanol was refluxed overnight for 17 hours. Evaporation of the reaction mixture in vacuo gave a residual oil which was crystallized by trituration with water. The crude yellow solid was recrystallized from methanol-water to give 1.61 g (90.1%), mp 185°-188°, of crystalline product. The analytical sample was obtained by recrystallization from methanol-water; yield, 1.36 g (76.9%); mp 188°-191°.

Workup

  1. temperaturewas refluxed overnight for 17 hours
  2. customEvaporation of the reaction mixture in vacuo
  3. customgave a residual oil which
  4. customwas crystallized by trituration with water
  5. customThe crude yellow solid was recrystallized from methanol-water
  6. customto give 1.61 g (90.1%), mp 185°-188°
  7. customyield

Sources & evidence

ORD record
ord-f8cf54e37038421f94532b3d4bf11d72
Source dataset
uspto-grants-1976_02
Patent number
US03936454

Reaction notes

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