Triethylamine → N-(2-Hydroxy-ethyl)-N-(4-oxo-3,5,7,8-tetrahydro-4H-pyrano[4,3-d]pyrimidin-2-ylmethyl)-3-phenyl-propionamide

HRID 588714Notes

Reaction equation

HRID 588714 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]1[NH:14][C:15](=[O:23])[C:16]2[CH2:22][O:21][CH2:20][CH2:19][C:17]=2[N:18]=1)(C(C)(C)C)(C)C.[C:24]1([CH2:30][CH2:31][C:32](Cl)=[O:33])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>ClCCl>[OH:8][CH2:9][CH2:10][N:11]([CH2:12][C:13]1[NH:14][C:15](=[O:23])[C:16]2[CH2:22][O:21][CH2:20][CH2:19][C:17]=2[N:18]=1)[C:32](=[O:33])[CH2:31][CH2:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 2724141Tetrabutylammonium FluorideHCID 1366299952-((2-(tert-Butyldimethylsilyloxy)ethylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one

Product 1

HCID 136232632N-(2-Hydroxy-ethyl)-N-(4-oxo-3,5,7,8-tetrahydro-4H-pyrano[4,3-d]pyrimidin-2-ylmethyl)-3-phenyl-propionamideYield 22.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-((2-(tert-butyldimethylsilyloxy)ethylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one (10 mg, 0.029 mmol) in dichloromethane (0.1 mL) was added 3-phenylpropanoyl chloride (4.4 μL, 0.029 mmol) and then triethylamine (12 μL, 0.088 mmol) at 0° C. The mixture was stirred at 0° C. to ambient temperature for 24 h. Tetra-N-butylammonium fluoride (29 μL, 0.029 mmol, 1 M in THF) was added and the reaction was stirred at ambient temperature for 1 h. The mixture was concentrated in vacuo then purified via prep thin layer chromatography to provide the title compound (2.3 mg, 22% yield). 1H NMR (400 MHz, CDCl3) δ 7.18-7.34 (m, 3H), 7.14 (d, J=7.5 Hz, 2H), 4.56 (s, 2H), 4.38 (s, 2H), 3.95 (t, J=5.5 Hz, 2H), 3.65-3.82 (m, 2H), 3.58 (t, J=4.5 Hz, 2H), 2.87-3.06 (m, 2H), 2.81 (t, J=7.5 Hz, 2H), 2.67 (br. s., 2H). HRMS calculated for C19H23N3O4 358.1767. found (ESI, [M+H]+), 358.1767. Retention time=0.99 min.

Workup

  1. customat 0° C
  2. stirringthe reaction was stirred at ambient temperature for 1 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customthen purified via prep thin layer chromatography

Sources & evidence

ORD record
ord-3b7e4b680ad141519010dcef0e4f1f9a
Source dataset
uspto-grants-2016_01
Patent number
US09227982B2

Reaction notes

Loading…