Triethylamine → 1-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-pyrimidin-acetic acid ethyl ester

HRID 48572Notes

Reaction equation

HRID 48572 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:24]([O:25][CH3:26])=[CH:23][C:7]([CH2:8][CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[CH2:12][CH2:11]N2)=[CH:6][CH:5]=1.[CH2:27](N(CC)CC)C.[CH2:34]([O:36][C:37](=[O:46])[CH2:38][C:39]1[N:44]=[C:43](Br)[CH:42]=[CH:41][N:40]=1)[CH3:35]>CN(C=O)C.CCOC(C)=O>[CH2:34]([O:36][C:37](=[O:46])[CH2:38][CH:39]1[N:44]=[CH:43][CH:42]=[CH:41][N:40]1[CH:27]1[CH2:11][CH2:12][C:13]2[C:18](=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH:9]1[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[C:24]([O:25][CH3:26])[CH:23]=1)[CH3:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 16667431Isoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-, hydrochloride (1:1)HCID 86589656Bromo-pyrimidin-acetic acid ethyl ester

Product 1

HCID 698959611-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-pyrimidin-acetic acid ethyl esterYield 63.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a white suspension of 1-(4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-hydrochloride (1.65 g, 4.36 mmol) in dry DMF (5 ml), were added triethylamine (1.82 ml, 0.013 mol) and bromo-pyrimidin-acetic acid ethyl ester (1.07 g, 4.36 mmol). The reaction mixture was stirred at reflux under argon for 20 h. After cooling, the mixture was diluted in AcOEt and washed with water. The aqueous phase was extracted twice with CH2Cl2, the combined organic phases were dried over anhydrous AcOEt, filtered and concentrated to give a crude brown-orange oil. Flash chromatography (AcOEt) gave 1.4 g (63%) of the title product as a brown-orange oil.

Workup

  1. temperatureat reflux under argon for 20 h
  2. temperatureAfter cooling
  3. washwashed with water
  4. extractionThe aqueous phase was extracted twice with CH2Cl2
  5. dry with materialthe combined organic phases were dried over anhydrous AcOEt
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude brown-orange oil

Sources & evidence

ORD record
ord-dd524a47efea4dbfbf4d5c16e487e8d6
Source dataset
uspto-grants-2004_03
Patent number
US06703392B2

Reaction notes

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