Triethylamine → HCID 21473642, compound

HRID 2294022Notes

Reaction equation

HRID 2294022 reaction equation
Cl.Cl[CH2:3][C:4]1[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=1.[CH2:12]([C:20]1[CH2:21][CH2:22][NH:23][CH2:24][CH:25]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>CN(C)C=O>[CH3:10][C:7]1[N:6]=[C:5]([NH2:11])[C:4]([CH2:3][N:23]2[CH2:22][CH:21]=[C:20]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:25][CH2:24]2)=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 214736115-(Chloromethyl)-2-methylpyrimidin-4-amine--hydrogen chloride (1/1)HCID 21473648HCID 21473648, compound

Product 1

HCID 21473642HCID 21473642, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A warm solution of 0.5 g (0.0026 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine hydrochloride in 40 ml of dimethylformamide was treated with 0.4 g (0.0021 mol) of 4-phenethyl-1,2,3,6-tetrahydro-pyridine and 0.9 ml (0.0064 mol) of triethylamine and the mixture was stirred at room temperature for 24 hours. The mixture was completely freed from the solvents. The residue was partitioned between dichloromethane and water, extracted, chromatographed over silica gel with acetonitrile/ethanol 8:1 as the eluent and digested in diethyl ether. 0.18 g (22%) of 2-methyl-5-(4-phenethyl-3,6-dihydro-2H-pyridin-1-ylmethyl)-pyrimidin-4-ylamine was obtained as white crystals; m.p. 152°-154°. A further 0.03 g of yellowish crystals was recovered from the mother liquor.

Workup

  1. customThe residue was partitioned between dichloromethane and water
  2. extractionextracted
  3. customchromatographed over silica gel with acetonitrile/ethanol 8:1 as the eluent and digested in diethyl ether

Sources & evidence

ORD record
ord-fc09acc616d5487192d46b8a8aae723e
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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