Sodium hydride → 1-(4-Amino-6-(methylthio)-1,3,5-triazin-2-yl)ethanol

HRID 1845867Notes

Reaction equation

Cl.[OH:2][CH:3]([CH3:7])[C:4](=[NH:6])[NH2:5].[H-].[Na+].[C:10]([N:12]=[C:13](SC)[S:14][CH3:15])#[N:11]>CN(C)C=O>[NH2:11][C:10]1[N:12]=[C:13]([S:14][CH3:15])[N:5]=[C:4]([CH:3]([OH:2])[CH3:7])[N:6]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Under a nitrogen atmosphere 2-hydroxypropanimidamide hydrochloride (4.97 g) was suspended in dry N,N-dimethylformamide (25 mL) and sodium hydride (1.66 g, 60 wt % in mineral oil) was added in one portion. When gas evolution ceased the white suspension was heated to 65° C. After 1 h dimethyl cyanocarbonimidodithioate (6.24 g) was added and the mixture was stirred at 65° C. for 18 hours. The reaction mixture was concentrated and triturated with water (200 mL). The resulting precipitate was filtered off, washed with water and the aqueous layer was extracted with 5% methanol in dichloromethane (3×100 mL). The combined organic extracts were dried (sodium sulfate) and concentrated before being purified by flash chromatography eluting with 10% methanol in dichloromethane to give the title compound (300 mg) as a yellow oil that solidified on standing.

Workup

concentrationThe reaction mixture was concentrated
customtriturated with water (200 mL)
filtrationThe resulting precipitate was filtered off
washwashed with water
extractionthe aqueous layer was extracted with 5% methanol in dichloromethane (3×100 mL)
dry with materialThe combined organic extracts were dried (sodium sulfate)
concentrationconcentrated
custombefore being purified by flash chromatography
washeluting with 10% methanol in dichloromethane

Sources & evidence

ORD record: ord-2bbc8ec5401b4bc1b1c6e6b37d32914b
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952001B2

Reaction notes

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