1,2,3,4-Tetrahydroisoquinoline → HCID 50996795, compound

HRID 1399609Notes

Reaction equation

HRID 1399609 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=1.[CH2:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26][NH:25]1.C(N(CC)CC)C>O1CCCC1>[CH2:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26][N:25]1[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 8471TriethylamineHCID 86665647Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 50996795HCID 50996795, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared according to the method C from methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.095 g; 0.285 mmol), 1,2,3,4-tetrahydroisoquinoline (0.108 mL; 0.856 mmol) and triethyl amine (0.200 mL; 1.43 mmol) in tetrahydrofuran (2 mL). Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-30%) in heptane furnished 0.072 g (58%) of the titled compound as a colorless oil.

Workup

  1. customThis compound was prepared
  2. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-30%) in heptane

Sources & evidence

ORD record
ord-2253507752ee41ec93045869f1554a71
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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