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Oxalyl chloride → 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-1,2,4-triazine-4-yl)amide

HRID 2381974
ノート
印刷プレビュー

反応式

HRID 2381974 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:12]=[CH:11][C:10]([C:13]([OH:15])=O)=[CH:9][N:8]=1.C(Cl)(=O)C(Cl)=O.[NH2:22][N:23]1[CH2:28][C:27]([CH3:29])=[N:26][NH:25][C:24]1=[O:30].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH3:29][C:27]1[CH2:28][N:23]([NH:22][C:13]([C:10]2[CH:11]=[N:12][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[N:8][CH:9]=2)=[O:15])[C:24](=[O:30])[NH:25][N:26]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 109755004-Amino-6-methyl-2,5-dihydro-1,2,4-triazin-3-oneHCID 249036332-(Pyridin-2-yl)pyrimidine-5-carboxylic acid

生成物 1

HCID 250997752-pyridin-2-yl-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-1,2,4-triazine-4-yl)amide収率 23%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (0.152 g, 0.75 mmol), in dry DCM (3 mL) and DMF (0.9 μL) in a dry flask under N2 is added oxalyl chloride (74 μL, 0.86 mmol). The reaction mixture is stirred at rt for 1 h. The solvent is evaporated and toluene is added and evaporated three times. The residue is dissolved in dry DCM (3 mL), and a solution of 4-amino-6-methyl-4,5-dihydro-2H-1,2,4-triazin-3-one (0.77 g, 0.6 mmol) in DCM (5 mL) is added followed by the addition of DIPEA (0.14 mL, 0.79 mmol). The mixture is stirred at rt overnight, and then concentrated in vacuo. The residue is diluted with water and adjusted to pH ˜8.5 with saturated aqueous NaHCO3 solution. The resulting precipitate is filtered to afford 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-1,2,4-triazine-4-yl)amide (0.043 g, 23%). MS: 312 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 11.11 (s, 1H), 9.95 (s, 1H), 9.31 (s, 2H), 8.78 (d, 1H), 8.45 (d, 1H), 8.01 (tr, 1H), 7.58 (dd, 1H), 4.22 (2, 2H), 1.91 (s, 3H).

後処理

  1. customThe solvent is evaporated
  2. additiontoluene is added
  3. customevaporated three times
  4. dissolutionThe residue is dissolved in dry DCM (3 mL)
  5. stirringThe mixture is stirred at rt overnight
  6. concentrationconcentrated in vacuo
  7. additionThe residue is diluted with water
  8. filtrationThe resulting precipitate is filtered

出典と根拠

ORDレコード
ord-855052fa01ca4296a35859371d43f4e0
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08258130B2

反応ノート

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