Water → 2-Methylsulfanyl-4-(5-methylsulfanyl-pyridin-2-yl)-6-trifluoromethyl-pyrimidine

HRID 1767707Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][N:8]=1)=O.S(O)(O)(=O)=O.[CH3:23][S:24][C:25](=[NH:27])[NH2:26].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[CH3:23][S:24][C:25]1[N:27]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][N:8]=2)[CH:4]=[C:3]([C:2]([F:17])([F:16])[F:1])[N:26]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4,4,4-trifluoro-1-(5-methylsulfanyl-pyridin-2-yl)-butane-1,3-dione (0.600 g, 2.28 mmol) in glacial acetic acid (6 mL) was added 2-methyl 2-thiopseudourea sulphate (0.761 g, 2.74 mmol) and sodium acetate (0.224 g, 2.74 mmol). The reaction was heated to 120° C. under nitrogen for 21 hours. The reaction was allowed to cool before the addition of water (10 mL), leading to precipitation of a solid. The reaction mixture was poured onto water (10 mL) and stirred for 15 minutes at 22° C. The precipitate was filtered from the aqueous solution, washed with water, and dried in vacuo to yield the title compound as a grey solid: MS m/z 317 (M+1).

Workup

customleading to precipitation of a solid
additionThe reaction mixture was poured onto water (10 mL)
filtrationThe precipitate was filtered from the aqueous solution
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-0d8abb85d6774d678a8cde75fcc15953
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235560B2

Reaction notes

Loading…