Potassium Carbonate → 5-(1,4,5,6-Tetrahydropyrimidin-1-yl)-3-methyl-2-nitro aniline

HRID 1793729노트

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HRID 1793729 반응식
F[C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[NH:13]1[CH2:18][CH2:17][CH2:16][N:15]=[CH:14]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[N:15]1([C:2]2[CH:3]=[C:4]([CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=2)[NH2:7])[CH2:16][CH2:17][CH2:18][N:13]=[CH:14]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 1371051,4,5,6-TetrahydropyrimidineHCID 220210255-Fluoro-3-methyl-2-nitroaniline

생성물 1

HCID 235418765-(1,4,5,6-Tetrahydropyrimidin-1-yl)-3-methyl-2-nitro aniline수율 67.2%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
100 °C

실험 절차

To a stirred solution of 2.0 g (11.76 mmol) of the 5-Flouro-3-methyl-2-nitro aniline in 10 mL of DMSO was added 1.2 g (14.11 mmol) of 1,4,5,6-Tetrahydropyrimidine, and 2.43 g (17.64 mmol) of potassium carbonate, and the mixture was heated at 100° C. for 10 hrs, cooled, diluted with water, and extracted with Ethylacetate containing 5% methanol. The combined organic extract was washed with water, brine and dried (Na2SO4). Evaporation of the solvent furnished the residue, which was chromatographed (20% of 2M ammonia in methanol and dichloromethane) to produce 1.85 g (67%) of the product as red solid. 1H NMR (400 MHz, CD3OD) δ 7.89 (1H,s), 6.53 (1H,d, J=2.57 Hz), 6.44 ((1H, d, J=2.1 Hz), 7.04 (1H, d, J=2.1 Hz), 3.70 (2H, t, J=6.0 Hz), 3.41 (2H, t, J=5.65 Hz, 2.43 (3H, s), 2.05 (2H, m) LCMS (M+H)+ m/z 235 (t=0.78 min).

후처리

  1. temperaturecooled
  2. extractionextracted with Ethylacetate containing 5% methanol
  3. extractionThe combined organic extract
  4. washwas washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent
  7. customfurnished the residue, which
  8. customwas chromatographed (20% of 2M ammonia in methanol and dichloromethane)

출처 및 근거

ORD 기록
ord-d952351fe42b4cd2974808a923bc8333
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07081454B2

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