Dimethyl Sulfate → HCID 13772019, compound

HRID 980888Notes

Reaction equation

HRID 980888 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.[CH2:8]([N:15]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:28][CH3:29])[C:22]=2[O:26][CH3:27])[NH:17][C:16]1=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[K+]>>[CH2:8]([N:15]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:28][CH3:29])[C:22]=2[O:26][CH3:27])[N:17]([CH3:16])[C:7]1=[O:6])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium Hydroxide2×HCID 13772015HCID 13772015, compound

Product 1

HCID 13772019HCID 13772019, compound

Conditions

Temperature
80 °C

Procedure

Dimethyl sulfate (1.442 g, 1.08 ml, 11.43 mM) was added to 3-benzyl-5,6-dimethoxyquinazolin-2,4(1H, 3H)-dione (1.20 g, 3.7 mM). The mixture was heated to 80° C. (oil bath temperature) and then heated at 80°-84° C. for five minutes with vigorous stirring. A white solid was present at all times. Aqueous KOH (~15 ml of a 5N aqueous solution) was added dropwise at 80°-90° C. until the pH of the reaction mixture became basic and stayed basic. Addition of the aqueous KOH took ~20 minutes. A white solid was present during the addition. The mixture was cooled in an ice-H2O bath and the white solid filtered, washed well with H2O (20 ml) and dried to give 1.00 g crude product. mp 149°-152° C. Recrystallization from isopropanol (50 ml) afforded the title compound as a white solid; 0.80 g (66.1%); mp 153°-155° C. CDCl3 (TMS) 7.10-7.80 (m, 6H, 7-H, 10-H, 11-H, 12-H, 13-H, 14-H), 6.82 (d, 1H, J8,7 =10 Hz, 8-H), 5.25 (s, 2H, 9-H), 3.95 (s, 3H, 5 or 6-OCH3), 3.88 (s, 3H, 5 or 6-OCH3), 3.53 (s, 3H, 1-CH3), M+ 326.

Workup

  1. temperatureheated at 80°-84° C. for five minutes with vigorous stirring
  2. waittook ~20 minutes
  3. additionA white solid was present during the addition
  4. temperatureThe mixture was cooled in an ice-H2O bath
  5. filtrationthe white solid filtered
  6. washwashed well with H2O (20 ml)
  7. customdried
  8. customto give 1.00 g crude product
  9. customRecrystallization from isopropanol (50 ml)

Sources & evidence

ORD record
ord-e79c1e491e804b6fba1962962a569062
Source dataset
uspto-grants-1987_01
Patent number
US04639518

Reaction notes

Loading…