Water → 2-(4-Methoxy-3,5-dimethylphenyl)-5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidine

HRID 81500Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[O:11][C:12]3[N:13]=[C:14]([S:20][CH3:21])[N:15]=[C:16]([OH:19])[C:17]=3[N:18]=2)=[CH:5][C:4]=1[CH3:22].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][CH3:32].O>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([CH3:22])=[CH:5][C:6]([C:10]2[O:11][C:12]3[N:13]=[C:14]([S:20][CH3:21])[N:15]=[C:16]([O:19][CH2:30][CH2:31][CH3:32])[C:17]=3[N:18]=2)=[CH:7][C:8]=1[CH3:9]

Participants

Conditions

Temperature: 60 °C

Procedure

5.9 g of 2-(4-methoxy-3,5-dimethylphenyl)-5-methylsulfanyloxazolo[5,4-d]pyrimidin-7-ol were dissolved in 150 ml of N,N-dimethylformamide, and 7.7 g of potassium carbonate and then 2.7 g of 1-bromopropane were added. The solution was stirred at 60° C. for 5 h and then, after cooling, poured into 150 ml of water. The precipitate was filtered off with suction. The regioisomer mixture obtained was purified by silica gel chromatography (50 g silicon dioxide solute cartridge, heptane/ethyl acetate 9/1). In addition to 1.4 g of 2-(4-methoxy-3,5-dimethylphenyl)-5-methylsulfanyl-6-propyl-6H-oxazolo[5,4-d]pyrimidin-7-one (LC/MS (Method LC1): Rt=1.43 min; m/z=360.13 [M+H]+), 2.5 g of the title compound were obtained.

Workup

temperatureafter cooling
filtrationThe precipitate was filtered off with suction
customThe regioisomer mixture obtained
customwas purified by silica gel chromatography (50 g silicon dioxide solute cartridge, heptane/ethyl acetate 9/1)
additionIn addition to 1.4 g of 2-(4-methoxy-3,5-dimethylphenyl)-5-methylsulfanyl-6-propyl-6H-oxazolo[5,4-d]pyrimidin-7-one (LC/MS (Method LC1): Rt=1.43 min; m/z=360.13 [M+H]+)

Sources & evidence

ORD record: ord-66c7ea0e04ad4981aaff8f7a3dd08b15
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846691B2

Reaction notes

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