1,2,3,4-Tetrahydroisoquinoline → 6-Ethyl-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2-chloropyrimidine

HRID 1289541Notes

Reaction equation

HRID 1289541 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.C(N(CC)CC)C.[CH2:18]([C:20]1[N:25]=[C:24]([Cl:26])[N:23]=[C:22](Cl)[CH:21]=1)[CH3:19]>CN(C)C=O>[CH2:18]([C:20]1[N:25]=[C:24]([Cl:26])[N:23]=[C:22]([N:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)[CH:21]=1)[CH3:19]

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 8471TriethylamineHCID 2460102,4-Dichloro-6-ethylpyrimidine

Product 1

HCID 189217966-Ethyl-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2-chloropyrimidineYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In accordance with the same procedure as in Step 1 of Example 1, except that 1,2,3,4-tetrahydroisoquinoline(3.5 ml, 28 mmol), triethylamine(3.9 ml, 28 mmol),N,N-dimethylformamide (20 ml) and 6-ethyl-2,4-dichloropyrimidine(4.9 g, 27.7 mmol) prepared in Preparation 2 were used as starting materials, 5.0 g of the titled compound was prepared. (Yield: 66%)

Sources & evidence

ORD record
ord-45412ff82e654b01ab528b716b17c3fd
Source dataset
uspto-grants-1998_05
Patent number
US05750531

Reaction notes

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