Sodium Hydroxide → 2-(Methylthio)-6-phenylpyrimidine-4-carboxylic acid

HRID 68297

反応式

HRID 68297 の反応式
O=[C:2]([CH2:6][C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4].S(O)(O)(=O)=O.[CH3:20][S:21][C:22](=[NH:24])[NH2:23].[O-]CC.[Na+].[OH-].[Na+]>C(O)C>[CH3:20][S:21][C:22]1[N:24]=[C:2]([C:3]([OH:5])=[O:4])[CH:6]=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:23]=1

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 4934182,4-Dioxo-4-phenylbutanoic acidHCID 2723922Sodium ethoxide

生成物 1

HCID 393492022-(Methylthio)-6-phenylpyrimidine-4-carboxylic acid収率 89.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 2,4-dioxo-4-phenylbutanoic acid (19.2 g, 100 mmol), 2-methylisothiourea sulfate (27.8 g, 100 mmol) and sodium ethoxide (37 mL, 21% wt. solution, 100 mmol) in ethanol (200 mL) was heated to reflux overnight. After removal of volatiles, water was added (200 mL) to give a suspension, which was adjusted to pH>9 with 10% NaOH. The mixture was extracted with diethyl ether (2×100 mL). The aqueous layer was taken to pH=2 with conc. HCI and extracted with diethyl ether (4×100 mL). The combined ethereal extracts were evaporated, and the residue was dried in vacuo overnight to afford 22.0 g of 2-methylsulfanyl-6-phenylpyrimidine-4-carboxylic acid as a yellow solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.24 (dd, J=7.8, 1.8 Hz, 2H), 8.12 (s, 1H), 7.58 (m, 3H), 2.64 (s, 3H). 13C NMR (DMSO-d6, 75 MHz) δ 172.8, 165.7, 165.6, 157.9, 135.8, 132.5, 129.8, 128.0, 14.6. HPLC ret. time 1.95 min, 10-100% CH3CN, 5 min run. ESI-MS m/z 247.1 (M+H)+.

後処理

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customAfter removal of volatiles, water
  4. additionwas added (200 mL)
  5. customto give a suspension, which
  6. extractionThe mixture was extracted with diethyl ether (2×100 mL)
  7. extractionextracted with diethyl ether (4×100 mL)
  8. customThe combined ethereal extracts were evaporated
  9. customthe residue was dried in vacuo overnight

出典と根拠

ORDレコード
ord-8a87e66f19304372b59d7f72ef175f3e
出典データセット
uspto-grants-2014_09
特許番号
US08822451B2

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