1,2,3,4-Tetrahydroisoquinoline → HCID 66955330, compound

HRID 1399642Notes

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.Cl[C:19]1[C:24]([CH:25]([CH2:30][CH2:31][CH3:32])[C:26]([O:28][CH3:29])=[O:27])=[C:23]([CH3:33])[N:22]=[C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:20]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:19]1[C:24]([CH:25]([CH2:30][CH2:31][CH3:32])[C:26]([O:28][CH3:29])=[O:27])=[C:23]([CH3:33])[N:22]=[C:21]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1,2,3,4-tetrahydroisoquinoline (0.190 mL, 1.5 mmol) and triethylamine (0.277 mL; 2 mmol) were added to a solution of methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.159 g; 0.5 mmol) in tetrahydrofuran (1.5 mL) and heated in a sealed tube to 100° C. for 18 h. The mixture was diluted with a saturated solution of sodium hydrogen carbonate and extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane furnished 0.194 g (93%) of the title compound.

Workup

extractionextracted with ethyl acetate
washThe combined organics were washed with brine
dry with materialdried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane

Sources & evidence

ORD record: ord-459e1071715f4c57a58d098b848b456d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906906B2

Reaction notes

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