Hydrochloric Acid → 6-Hydroxy-2-(methylthio)-4-pyrimidinecarboxylic acid

HRID 68300

反応式

HRID 68300 の反応式
[C:1]([O:11]CC)(=O)[CH2:2][C:3]([C:5]([O:7]CC)=[O:6])=O.[OH-].[Na+].S(O)(O)(=O)=O.[CH3:21][S:22][C:23](=[NH:25])[NH2:24].Cl>O>[CH3:21][S:22][C:23]1[NH:25][C:1](=[O:11])[CH:2]=[C:3]([C:5]([OH:7])=[O:6])[N:24]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66951Diethyl oxalacetateHCID 752702-Methyl-2-thiopseudourea sulfate

生成物 1

HCID 1354730056-Hydroxy-2-(methylthio)-4-pyrimidinecarboxylic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Neat diethyl oxalacetate (23.5 g, 125 mmol) was added to a solution of sodium hydroxide (15 g, 0.375 mol, 3 eq) in water (150 mL), giving a yellow solution. Solid S-methylisothiourea sulfate (17.4 g, 62.5 mmol, 0.5 eq) was added to the stirred solution. The mixture was stirred 15 hours. Concentrated HCl (40 mL, 0.48 mol) was added bringing the pH to 1, the resultant pale orange-pink suspension was stirred vigorously for 2 hours then filtered. The filter cake was washed with water (100 mL), and dried under high vacuum to afford 2-methylsulfanyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid as an off-white solid. 1H NMR (500 MHz, DMSO-d6) □ 13.22 (br s, 1H), 6.60 (s, 1H), 3.37 (br s, 1H), 2.53 (s, 3H); ESI-MS m/z 186.9 (M+H)+.

後処理

  1. customgiving a yellow solution
  2. stirringthe resultant pale orange-pink suspension was stirred vigorously for 2 hours
  3. filtrationthen filtered
  4. washThe filter cake was washed with water (100 mL)
  5. customdried under high vacuum

出典と根拠

ORDレコード
ord-72d00958ca7a4a64a7aeba9f751d92d5
出典データセット
uspto-grants-2014_09
特許番号
US08822451B2

関連ノート

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