Triethylamine → HCID 21473620, compound

HRID 2294053Notes

Reaction equation

HRID 2294053 reaction equation
Cl.Cl[CH2:3][C:4]1[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=1.Cl.[Cl:13][C:14]1[CH:15]=[C:16]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH2:27][NH:26][CH2:25][CH2:24]3)[CH:17]=[C:18]([Cl:20])[CH:19]=1.C(N(CC)CC)C>CN(C)C=O>[Cl:13][C:14]1[CH:15]=[C:16]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH2:27][N:26]([CH2:3][C:4]2[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=2)[CH2:25][CH2:24]3)[CH:17]=[C:18]([Cl:20])[CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 214736115-(Chloromethyl)-2-methylpyrimidin-4-amine--hydrogen chloride (1/1)HCID 21473658HCID 21473658, compound

Product 1

HCID 21473620HCID 21473620, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.85 g (0.0095 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine hydrochloride in 105 ml of dimethylformamide was treated with 250 g (0.00795 mol) of 6-(3,5-dichlorophenyl)-1,2,3,4-tetrahydro-isoquinoline hydrochloride and 3.66 ml (0.026 mol) of triethylamine and stirred at room temperature under argon for 65 hours. The mixture was completely freed from the solvents. The residue was partitioned between dichloromethane and water. 30 ml of a 1N aqueous sodium hydroxide solution were added dropwise thereto, the mixture was extracted and chromatographed over silica gel with ethyl acetate/isopropyl alcohol 9:1 as the eluent. Crystallization was then carried out, firstly from methanol/ethyl acetate/n-hexane and then from hot ethyl acetate. 1.21 g (38%) of 5-[6-(3,5-dichlorophenyl)-3,4-dihydro-1H-isoquinolin-2-ylmethyl]-2-methyl-pyrimidin-4-ylamine were obtained as white crystals; m.p. 205°-211°.

Workup

  1. customThe residue was partitioned between dichloromethane and water
  2. addition30 ml of a 1N aqueous sodium hydroxide solution were added dropwise
  3. extractionthe mixture was extracted
  4. customchromatographed over silica gel with ethyl acetate/isopropyl alcohol 9:1 as the eluent
  5. customCrystallization

Sources & evidence

ORD record
ord-4dc4043177bb4cfda2417f03e91ad513
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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