4-(1-(2-Chlorophenoxy)ethyl)-6-(methylthio)-1,3,5-triazin-2-amine → 4-(1-(2-Chlorophenoxy)ethyl)-1,3,5-triazin-2-amine

HRID 1845877Notes

Reaction equation

[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[O:4][CH:5]([C:7]1[N:12]=[C:11](SC)[N:10]=[C:9]([NH2:15])[N:8]=1)[CH3:6]>C(O)C.[Ni]>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[O:4][CH:5]([C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH2:15])[N:8]=1)[CH3:6]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 4-(1-(2-chlorophenoxy)ethyl)-6-(methylthio)-1,3,5-triazin-2-amine (16a) (181 mg) in ethanol (10 mL) was added. Raney-nickel was added via a syringe (2.0 mL) and the reaction mixture was heated at 85° C. for 40 minutes then cooled to room temperature and the mixture was filtered over Celite and washed with ethanol/water (1/1 v/v) and methanol. The filtrate was concentrated in vacuo and further purified by column chromatography (eluting with 1% acetontrile in dichloromethane) to give the title compound (25 mg), MS (ES): m/z 251 [M+H]+.

Workup

temperaturethen cooled to room temperature
filtrationthe mixture was filtered over Celite
washwashed with ethanol/water (1/1 v/v) and methanol
concentrationThe filtrate was concentrated in vacuo
customfurther purified by column chromatography (eluting with 1% acetontrile in dichloromethane)

Sources & evidence

ORD record: ord-f8f085edd42242acb9ff1f476e3d6a07
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952001B2

Reaction notes

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