Citric Acid → 2-(2-(Methylthio)pyrimidin-4-yl)-3-oxopropanenitrile

HRID 500707Notes

Reaction equation

[O:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][N:9]=[C:8]([S:12][CH3:13])[N:7]=2)[CH:3]=[N:2]1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.CO>[CH3:13][S:12][C:8]1[N:7]=[C:6]([CH:4]([CH:5]=[O:1])[C:3]#[N:2])[CH:11]=[CH:10][N:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-(isoxazol-4-yl)-2-(methylthio)pyrimidine (4) (112.0 g, 0.58 mol) and NaOH (23.2 g) in water/MeOH (350 mL/350 mL) was stirred at 70° C. for 6 h. The reaction mixture was allowed to cool to room temperature and adjusted to pH 3.5 with citric acid. The resulting precipitate was filtered, washed with water (500 mL×3) and ethyl ether (500 mL×3). Then the precipitate was dried in vacuum to give 2-(2-(methylthio)pyrimidin-4-yl)-3-oxopropanenitrile (5) (100 g, 89.3%) as a yellow solid.

Workup

temperatureto cool to room temperature
filtrationThe resulting precipitate was filtered
washwashed with water (500 mL×3) and ethyl ether (500 mL×3)
customThen the precipitate was dried in vacuum

Sources & evidence

ORD record: ord-7d23fa819ee1442baeb58e71e7f68888
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772246B2

Reaction notes

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