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

HRID 1247651Notes

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 (prepared according to WO 00/24744) were dissolved in 30 mL THF. 14 mL of a 1.4 M solution of methyl magnesium bromide in ether were added drop-wise 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-28015d3f512f4801bacb1890b0d63d0f
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129351B2

Reaction notes

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