Water → HCID 67175754, compound

HRID 1626020Notes

Reaction equation

HRID 1626020 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[C:5]([OH:19])[C:6]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=3)[O:9][C:7]=2[N:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH3:29].O>CN(C)C=O>[CH3:1][S:2][C:3]1[N:4]([CH2:27][CH2:28][CH3:29])[C:5](=[O:19])[C:6]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=3)[O:9][C:7]=2[N:8]=1.[CH3:1][S:2][C:3]1[N:4]=[C:5]([O:19][CH2:27][CH2:28][CH3:29])[C:6]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=3)[O:9][C:7]=2[N:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 178503523HCID 178503523, compound

Product 2

HCID 67175754HCID 67175754, compoundHCID 67176099HCID 67176099, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

7.1 g of 5-methylsulfanyl-2-(3-methyl-phenyl)-oxazolo[5,4-d]pyrimidin-7-ol were dissolved in 50 ml of dimethylformamide, and 14.4 g of potassium carbonate and then 3.2 g of 1-bromo-propane were added. The suspension was stirred at 60° C. for 5 h and then, after cooling, poured onto 150 ml of water. The precipitate was filtered off with suction. The obtained mixture of regioisomers was separated by silica gel chromatography (heptane/ethyl acetate gradient). Besides 2.3 g of 5-methylsulfanyl-6-propyl-2-(3-methyl-phenyl)-6H-oxazolo[5,4-d]pyrimidin-7-one (LC/MS (method LC1): Rt=2.16 min; m/z=316.14 [M+H]+), 3.4 g of the title compound were obtained.

Workup

  1. temperatureafter cooling
  2. filtrationThe precipitate was filtered off with suction
  3. additionThe obtained mixture of regioisomers
  4. customwas separated by silica gel chromatography (heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-e98c5365c4a1490d88cf4fcddfa3d94d
Source dataset
uspto-grants-2014_07
Patent number
US08785439B2

Reaction notes

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