Triethylamine → 6-Methoxymethyl-5-methyl-2-chloro-4-(1-methyl-6-methoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

HRID 275950Notes

Reaction equation

HRID 275950 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1.C(N(CC)CC)C.[Cl:21][C:22]1[N:27]=[C:26](Cl)[C:25]([CH3:29])=[C:24]([CH2:30][O:31][CH3:32])[N:23]=1>CN(C)C=O>[CH3:32][O:31][CH2:30][C:24]1[N:23]=[C:22]([Cl:21])[N:27]=[C:26]([N:3]2[CH2:4][CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=3)[CH:2]2[CH3:1])[C:25]=1[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 142302816-Methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolineHCID 183158422,4-Dichloro-6-methoxymethyl-5-methylpyrimidine

Product 1

HCID 183156576-Methoxymethyl-5-methyl-2-chloro-4-(1-methyl-6-methoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidineYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 1-methyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline(1.2 g, 6.8 mmol) and triethylamine(0.96 ml, 6.9 mmol) were added to a suspension of 2,4-dichloro-6-methoxymethyl-5-methylpyrimidine(1.3 g, 6.3 mmol) in dimethylformamide, 2.0 g of the titled compound was obtained in accordance with the same procedure as in Step 1 of Example 35. (Yield: 73.6%)

Sources & evidence

ORD record
ord-e19564dcb93e4352bc5104a7c44638c9
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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