2-Amino-4,6-dimethoxypyrimidine → HCID 13923718, compound

HRID 255835Notes

Reaction equation

HRID 255835 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([N:16]=[C:17]=[O:18])(=[O:15])=[O:14])(=[O:3])[CH3:2].[NH2:19][C:20]1[N:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[N:21]=1>C(#N)C>[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([NH:16][C:17]([NH:19][C:20]1[N:21]=[C:22]([O:28][CH3:29])[CH:23]=[C:24]([O:26][CH3:27])[N:25]=1)=[O:18])(=[O:15])=[O:14])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 15616510HCID 15616510, compound

Product 1

HCID 13923718HCID 13923718, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 2.3 g of the sulfonyl isocyanate from Example 7 in 25 ml dry acetonitrile was added 1.2 g of 2-amino-4,6-dimethoxypyrimidine. The reaction mixture was warmed to 50° C. for 11/4 hour and then stirred at room temperature for 2 days. Filtration of the insoluble solids and washing with 1-chlorobutane followed by drying afforded 1.8 g of 2-[2-(acetyloxy)ethyl]-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide as a light yellow solid, m.p. 160°-162° C.

Workup

  1. filtrationFiltration of the insoluble solids
  2. washwashing with 1-chlorobutane
  3. customby drying

Sources & evidence

ORD record
ord-9125cb95be464dd5b618a84b0d95ab93
Source dataset
uspto-grants-1987_10
Patent number
US04699650

Reaction notes

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