Hydroxyamine hydrochloride → 4-(2-(Methylthio)pyrimidin-4-yl)isoxazole

HRID 500706Notes

Reaction equation

Cl.[NH2:2]O.[OH:4]/[CH:5]=[C:6](\[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([S:15][CH3:16])[N:10]=1)/[CH:7]=O.C([O-])(O)=O.[Na+]>O>[O:4]1[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([S:15][CH3:16])[N:10]=2)[CH:7]=[N:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of hydroxylamine hydrochloride (60.0 g, 0.86 mol) in water (2 L) was added (E)-3-hydroxy-2-(2-(methylthio)pyrimidin-4-yl)acrylaldehyde (3) (342 g, 0.714 mol) in portions. After the addition, the mixture was heated at 60° C. and stirred for 2 h. The reaction mixture was allowed to cool to room temperature and the solution was adjusted to pH about 4 by addition of 10% aq. NaHCO3. The resulting precipitate was filtered, washed with water (200 mL×2) and dried in vacuum to give 4-(isoxazol-4-yl)-2-(methylthio)pyrimidine (4) (112 g, 81.2%) as a yellow solid.

Workup

additionAfter the addition
temperatureto cool to room temperature
filtrationThe resulting precipitate was filtered
washwashed with water (200 mL×2)
customdried in vacuum

Sources & evidence

ORD record: ord-6a07dc6b8e83431c8cc9eb505e61d4e6
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772246B2

Reaction notes

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