Acetic Anhydride → 1-{[o-(Cyclopropylhydroxymethyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea acetate

HRID 128533Notes

Reaction equation

HRID 128533 reaction equation
[C:1]([O:4]C(=O)C)(=[O:3])[CH3:2].[CH:8]1([CH:11]([OH:36])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][S:19]([NH:22][C:23]([NH:25][C:26]2[N:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([O:34][CH3:35])[N:27]=2)=[O:24])(=[O:21])=[O:20])[CH2:10][CH2:9]1.C(OCC)(=O)C>N1C=CC=CC=1.O>[C:1]([OH:4])(=[O:3])[CH3:2].[CH:8]1([CH:11]([OH:36])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][S:19]([NH:22][C:23]([NH:25][C:26]2[N:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([O:34][CH3:35])[N:27]=2)=[O:24])(=[O:21])=[O:20])[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 7918Acetic Anhydride2×HCID 8857Ethyl AcetateHCID 152786351-[(alpha-Cyclopropyl-alpha-hydroxy-o-tolyl)sulfamoyl]-3-(4,6-dimethoxy-2-pyrimidinyl)urea

Product 1

HCID 676897071-{[o-(Cyclopropylhydroxymethyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea acetateYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.18 mL, 0.19 g, 1.9 mmol) is added to a mixture of 1-[(α-cyclopropyl-α-hydroxy-o-tolyl)sulfamoyl]-3-(4,6-dimethoxy-2-pyrimidinyl)urea (0.40 g, 0.9 mmol) in pyridine. The reaction mixture is stirred at room temperature for 18 hours, treated with additional acetic anhydride (0.27 mL, 2.9 mmol), stirred for 5 hours, diluted with water and extracted with ether. The combined organic extracts are dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and 50% to 75% ethyl acetate in hexanes solutions gives the title product as a white powder (0.10 g, 23%, mp 156°-158° C.) which is identified by 1HNMR and MS spectral analyses.

Workup

  1. stirringstirred for 5 hours
  2. extractionextracted with ether
  3. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue

Sources & evidence

ORD record
ord-48e1ce5259de4fdfa476ebf896005404
Source dataset
uspto-grants-1995_11
Patent number
US05464808

Reaction notes

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