4-(Methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde → 1-(4-Methylamino-2-methylsulfanyl-pyrimidin-5-yl)-ethanol

HRID 9725Notes

Reaction equation

[CH3:1][NH:2][C:3]1[C:8]([CH:9]=[O:10])=[CH:7][N:6]=[C:5]([S:11][CH3:12])[N:4]=1.[CH3:13][Mg]Br>C1COCC1.CCOCC>[CH3:1][NH:2][C:3]1[C:8]([CH:9]([OH:10])[CH3:13])=[CH:7][N:6]=[C:5]([S:11][CH3:12])[N:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.5 g 4-Methylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde were dissolved in 30 ml THF and 14 ml of a 1.4 M solution of methyl magnesium bromide in ether were added dropwise below 5° C. After stirring for 1 hr at 0° C., another 14 ml Grignard solution were added within 30 min. Stirring was continued for 30 min at 0° C. and finally at RT for 25 hrs. The mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate.

Workup

additionanother 14 ml Grignard solution were added within 30 min
stirringStirring
waitwas continued for 30 min at 0° C. and finally at RT for 25 hrs
customThe mixture was quenched with saturated ammonium chloride solution
extractionextracted with ethyl acetate

Sources & evidence

ORD record: ord-c30e63ee47dc475e94aad2aa23ea7648
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091345B2

Reaction notes

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