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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
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HRID 2381974 반응식
[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
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참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-855052fa01ca4296a35859371d43f4e0
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08258130B2

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