Triethylamine → HCID 53772441, compound

HRID 2294025Notes

Reaction equation

HRID 2294025 reaction equation
Cl.Cl[CH2:3][C:4]1[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=1.[C:12]1([C:18]#[C:19][CH:20]2[CH:25]=[CH:24][NH:23][CH2:22][CH2:21]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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]([C:19]#[C:18][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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 70193131HCID 70193131, compound

Product 1

HCID 53772441HCID 53772441, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.19 g (0.00098 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine hydrochloride in 20 ml of dimethyl-formamide was treated with 0.15 g (0.82 mol) of 4-phenylethynyl-1,2,3,4-tetrahydro-pyridine and 0.34 ml (0.0024 mol) of triethylamine and the mixture was stirred at room temperature under argon for 16 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. 0.10 g (34%) of 2-methyl-5-(4-phenylethynyl-3,6-dihydro-2H-pyridin-1-ylmethyl)-pyrimidin-4-ylamine as white crystals; m.p. 187°-188°.

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-ca8e88443bbd40d3b128344ecd13aa26
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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