2-(Dimethylamino)ethanol → HCID 89656249, compound

HRID 626149Notes

Reaction equation

HRID 626149 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[CH:12][CH:11]=2)=[O:9])=[N:6][CH:7]=1.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][O:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[CH:14][CH:15]=2)=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 89655801HCID 89655801, compound

Product 1

HCID 89656249HCID 89656249, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (5-hydroxypyrimidin-2-yl)(4-(tetrahydro-2H-pyran-2-yloxy) phenyl)methanone (300 mg, 1 mmol), 2-(dimethylamino)ethanol (180 mg, 2 mmol) and PPh3 (524 mg, 2 mmol) in 50 mL of THF was added DIAD (404 mg, 2 mmol) dropwise and the mixture was stirred overnight at rt. The mixture was concentrated and purified by flash chromatography to give the product (297 mg, 80% yield)

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-6211f53bddb344adbec13835b5bce1d3
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

Loading…