Methane → 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic Acid

HRID 507542

反応式

HRID 507542 の反応式
[C:1]([OH:9])(=[O:8])/[C:2](=[C:4](\[CH:6]=O)/[Br:5])/Br.S(O)(O)(=O)=O.[CH3:15][S:16][C:17](=[NH:19])[NH2:18].C(N(CC)CC)C.C>O>[Br:5][C:4]1[C:2]([C:1]([OH:9])=[O:8])=[N:18][C:17]([S:16][CH3:15])=[N:19][CH:6]=1

参加物

6

反応物 4

HCID 297MethaneHCID 8471TriethylamineHCID 752702-Methyl-2-thiopseudourea sulfateHCID 3033972Mucobromic Acid

生成物 1

HCID 2917865-Bromo-2-(methylthio)pyrimidine-4-carboxylic Acid収率 59.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Mucobromic acid (58.05 g, 0.225 mol) was added to a stirred solution of 2-methyl-2-thio-pseudourea sulfate (62.66 g, 0.225 mol) in water (500 mL) at r.t. The suspension was cooled to 10° C. (ice bath) and triethylamine (94.1 mL, 0.675 mol) was added dropwise over 4 h. The reaction mixture was then left to stand at r.t. for 24 h. Activated carbon (Darco G-60) was added to the now dark red/brown solution and after stirring for 10 min the charcoal was filtered off. The filtrate was acidified with concentrated hydrochloric acid (50 mL) and the yellow precipitate was filtered off, washed with water (2×80 mL) and diethyl ether (2×100 mL), and then placed in a vacuum oven at 50° C. for 2 days to yield 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (33.13 g, 59%) as a yellow amorphous solid. 1H NMR δ (d6-DMSO, 400 MHz) 2.75 (s, 3H), 9.20 (s, 1H).

後処理

  1. additionwas added dropwise over 4 h
  2. waitThe reaction mixture was then left
  3. additionActivated carbon (Darco G-60) was added to the now dark red/brown solution
  4. filtrationwas filtered off
  5. filtrationthe yellow precipitate was filtered off
  6. washwashed with water (2×80 mL) and diethyl ether (2×100 mL)
  7. waitplaced in a vacuum oven at 50° C. for 2 days

出典と根拠

ORDレコード
ord-24445af16d2140b887645c7414873057
出典データセット
uspto-grants-2010_08
特許番号
US07786132B2

関連ノート

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