1,2-Dichloroethane → 4-Chloro-5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidine

HRID 19654

반응식

HRID 19654 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:18][CH2:17][C:11]3[N:12]=[CH:13][NH:14][C:15](=O)[C:10]=3[CH2:9]2)=[N:6][CH:7]=1.P(Cl)(Cl)([Cl:21])=O.ClCCCl.CN(C)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:21][C:15]1[C:10]2[CH2:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=3)[CH2:18][CH2:17][C:11]=2[N:12]=[CH:13][N:14]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 1359789575,6,7,8-Tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidin-4(3H)-one

생성물 1

HCID 593464574-Chloro-5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Into a 250 ml round bottom flask was combined 5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidin-4(3H)-one (0.250 g, 0.00103 mol), phosphoryl chloride (0.8 mL, 0.008 mol), and 1,2-dichloroethane (10 mL, 0.1 mol). N,N-Dimethylaniline (0.01 g, 0.0001 mol) was added dropwise and the mixture was heated at reflux for 2 hours. The mixture was reduced in vacuo to yield a dark brown oil. The oil was taken up in methylene chloride (50 ml) and poured over ice. The mixture was carefully neutralized using sat sodium bicarbonate. The layers were separated and the organic was dried over sodium sulfate and reduced in vacuo. The mixture was purified by flash chromatography on silica gel using methylene chloride:methanol (0-10%). The combined pure fractions were reduced in vacuo to yield a bright yellow solid. (0.141 g, 52.4%).

후처리

  1. customInto a 250 ml round bottom flask was combined
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 2 hours
  4. customto yield a dark brown oil
  5. additionpoured over ice
  6. customThe layers were separated
  7. dry with materialthe organic was dried over sodium sulfate
  8. customThe mixture was purified by flash chromatography on silica gel
  9. customto yield a bright yellow solid

출처 및 근거

ORD 기록
ord-9f90f4e8d2924805a4c684fe0ba3186c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745451B2

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