Acetic Acid → HCID 19860374, compound

HRID 1721877Notes

Reaction equation

[CH3:1][CH:2]([NH:4][C:5]([NH:7][S:8]([C:11]1[C:12]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=2)=[N:13][C:14](S(C)=O)=[N:15][CH:16]=1)(=[O:10])=[O:9])=[O:6])[CH3:3].[CH3:28][NH2:29].[OH-].[Na+].C(O)(=O)C>O.C(O)C>[CH3:28][NH:29][C:14]1[N:13]=[C:12]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=2)[C:11]([S:8]([NH:7][C:5]([NH:4][CH:2]([CH3:3])[CH3:1])=[O:6])(=[O:10])=[O:9])=[CH:16][N:15]=1

Participants

Conditions

Temperature: 45 °C

Procedure

N-[[(1-Methylethyl)amino]carbonyl]-4-[(3-methylphenyl)amino]-2-(methylsulfinyl)-5-pyrimidinesulfonamide (1.39 g, 3.38 mmol) was suspended in water (20 mL) and aqueous methylamine (6 mL, 40 wt % in H2O) was added to form a homogeneous solution. The mixture was stirred for five hours at 45° C., then diluted with an equal volume of ethanol and the solvents removed under reduced pressure to give a solid residue. The residue was suspended in water (20 mL) and 1.0N sodium hydroxide was added until the solution became homogeneous. Aqueous acetic acid 10% was added dropwise to form a white solid precipitate. The solid was filtered, washed three times, and dried in a vacuum oven at 75° C. overnight to yield 1.12 g (2.96 mmol, 88%) of pure product, m.p. 206°-207° C., as a white solid.

Workup

customto form a homogeneous solution
customthe solvents removed under reduced pressure
customto give a solid residue
customto form a white solid precipitate
filtrationThe solid was filtered
washwashed three times
customdried in a vacuum oven at 75° C. overnight

Sources & evidence

ORD record: ord-900d172fcbc940da85d5c0ef6b6e64cf
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04853389

Reaction notes

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