Dimethylformamide → HCID 59036093, compound

HRID 1393970Notes

Reaction equation

HRID 1393970 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.CN(C=O)C.Cl[CH2:15][CH2:16][N:17]1[C:22](=[O:23])[CH:21]=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:19]=[C:18]1[CH2:30][CH3:31]>>[CH2:30]([C:18]1[N:17]([CH2:16][CH2:15][S:8][C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[C:22](=[O:23])[CH:21]=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:19]=1)[CH3:31]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 2401474-MercaptophenolHCID 69216972HCID 69216972, compound

Product 1

HCID 59036093HCID 59036093, compound

Procedure

To 4-hydroxy thiophenol (2.016 g, 0.016 mol) in DMF (50 ml) K2CO3 (4.416 g, 0.032 mol) was added and stirred for 30 min. and then added 1-(2-chloroethyl)-2-ethyl-4-phenyl-1,6-dihydropyrimidin-6-one (4.3 g, 0.016 mol). The resulting mixture was stirred at room temperature for 15 h, filtered, washed with EtOAc and the combined filtrates were partitioned between water and EtOAc. The EtOAc layer was washed with water, brine, dried over Na2SO4 and evaporated the solvent to get the title compound as a gummy mass (1.25 g, 26%).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 15 h
  2. filtrationfiltered
  3. washwashed with EtOAc
  4. customthe combined filtrates were partitioned between water and EtOAc
  5. washThe EtOAc layer was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. customevaporated the solvent

Sources & evidence

ORD record
ord-f9ff5a6424c34382ba26fb811b3e0269
Source dataset
uspto-grants-2008_03
Patent number
US07348334B2

Reaction notes

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