Hydrochloric Acid → Methyl (4,6-dimethoxypyrimidin-2-yl)carbamate

HRID 1193446ノート

反応式

HRID 1193446 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[H-].[Na+].[CH3:14][O:15][C:16](=O)[O:17]C.Cl.[Cl-].[Na+]>O1CCCC1>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([NH:1][C:16](=[O:17])[O:15][CH3:14])[N:7]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 1189462-Amino-4,6-dimethoxypyrimidine

生成物 1

HCID 13314628Methyl (4,6-dimethoxypyrimidin-2-yl)carbamate収率 70.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

2-Amino-4,6-dimethoxypyrimidine (56 g) was added portionwise to 50% sodium hydride (42.8 g) in 1000 ml of dry tetrahydrofuran. After stirring for 0.5 hour, dimethylcarbonate (58.5 g) was added dropwise with cooling. The mixture was stirred under nitrogen for about 16 hours at ambient temperature. Concentrated HCl (80 ml) was added slowly as external cooling was used to maintain a pot temperature of about 25° C. Saturated aqueous sodium chloride (80 ml) was then added. The solvents were decanted from the precipitated solids and dried over sodium sulfate. Filtering and evaporating the solvents afforded the crude material which was recrystallized from hexane to yield 54 g of the title compound, m.p. 81°-83° C. The IR spectrum showed characteristic absorption bands at 3400 and 1760 cm-1.

後処理

  1. temperaturewith cooling
  2. stirringThe mixture was stirred under nitrogen for about 16 hours at ambient temperature
  3. temperatureas external cooling
  4. customThe solvents were decanted from the precipitated solids
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltering
  7. customevaporating the solvents
  8. customafforded the crude material which
  9. customwas recrystallized from hexane

出典と根拠

ORDレコード
ord-1975b6f7583340bc9c935df6d4355804
出典データセット
uspto-grants-1989_03
特許番号
US04810282

反応ノート

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