Phosphorus oxychloride → Methyl 5-chloro-3-(methylthio)pyrimido[4,5-c]quinoline-8-carboxylate

HRID 2174896노트

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HRID 2174896 반응식
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15]3[CH:14]=[CH:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]=3[NH:9][C:8](=O)[C:7]=2[N:21]=1.O=P(Cl)(Cl)[Cl:24].CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[Cl:24][C:8]1[C:7]2[N:21]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=2[C:15]2[CH:14]=[CH:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]=2[N:9]=1

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 57500644Methyl 3-(methylthio)-5-oxo-5,6-dihydropyrimido[4,5-c]quinoline-8-carboxylate

생성물 1

HCID 57500645Methyl 5-chloro-3-(methylthio)pyrimido[4,5-c]quinoline-8-carboxylate수율 63%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
120 °C

실험 절차

methyl 3-(methylthio)-5-oxo-5,6-dihydropyrimido[4,5-c]quinoline-8-carboxylate (1.0 eq, 279 mg, 0.926 mmol) was suspended in toluene (2 ml). POCl3 (2 ml) and DIEA (0.5 ml) were added and the mixture stirred at 120° C. for 5 hours. The volatiles were removed in vacuo and CH2Cl2 was added. The organic phase was washed with saturated aqueous sodium bicarbonate, washed with water and dried over Na2SO4. The solution was filtered through a pad of celite and the solvents removed in vacuo. The material was triturated in hexanes and AcOEt, filtered and dried to provide methyl 5-chloro-3-(methylthio)pyrimido[4,5-c]quinoline-8-carboxylate as a beige solid (184 mg, 63% yield). LCMS (ES): >95% pure, m/z 320 [M+1]+, 322 [M+3]+.

후처리

  1. customThe volatiles were removed in vacuo and CH2Cl2
  2. additionwas added
  3. washThe organic phase was washed with saturated aqueous sodium bicarbonate
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. filtrationThe solution was filtered through a pad of celite
  7. customthe solvents removed in vacuo
  8. customThe material was triturated in hexanes
  9. filtrationAcOEt, filtered
  10. customdried

출처 및 근거

ORD 기록
ord-f74dcbcc632642f9b75528de13143436
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062043B2

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