Acetic Acid → 2-(2,6-Dimethylphenyl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80764

반응식

HRID 80764 반응식
C([N:8]1[CH2:27][CH2:26][C:11]2[N:12]=[C:13]([C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:25])[N:14]=[C:15]([O:16][CH3:17])[C:10]=2[CH2:9]1)C1C=CC=CC=1.C(O)(=O)C>C1COCC1.O.[OH-].[OH-].[Pd+2]>[CH3:24][C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:25])[C:18]=1[C:13]1[N:14]=[C:15]([O:16][CH3:17])[C:10]2[CH2:9][NH:8][CH2:27][CH2:26][C:11]=2[N:12]=1

참가 물질

6

반응물 2

HCID 176Acetic AcidHCID 712447526-Benzyl-2-(2,6-dimethylphenyl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

생성물 1

HCID 712446992-(2,6-Dimethylphenyl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

시약·촉매·용매 3

HCID 9942167Palladium hydroxide촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6-benzyl-2-(2,6-dimethylphenyl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (7.08 g, 19.70 mmol) in THF (100 mL) and H2O (12.50 mL), was added 20% Pd(OH)2 wet (50% dry basis, 2.77 g, 1.970 mmol), followed by acetic acid (2.26 mL, 39.4 mmol). The reaction was stirred at r.t. under hydrogen atmosphere for 30 min, then heated to 40° C. for 16 h. The reaction mixture was cooled to r.t. and filtered through a Celite® pad which was washed with methanol. The organic solvent in the filtrate was removed under reduced pressure. The reaction mixture was diluted by 200 mL DCM and neutralized by saturated aqueous NaHCO3. The mixture was extracted twice by DCM. The combined organic layers were dried over Na2SO4. After filtration and concentration, the resulting residue was purified via silica gel FCC (Methanol/DCM=0 to 10%) to provide 2-(2,6-dimethylphenyl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.14-7.22 (m, 1 H), 7.05-7.11 (m, 2 H), 5.75 (s, 1 H), 3.88 (s, 3 H), 3.72 (s, 2 H), 3.01 (t, J=5.8 Hz, 2 H), 2.68 (t, J=5.7 Hz, 2 H), 2.03 (s, 6 H). MS (ESI+) m/z 270.5 (M+H)+.

후처리

  1. temperatureheated to 40° C. for 16 h
  2. temperatureThe reaction mixture was cooled to r.t.
  3. filtrationfiltered through a Celite® pad which
  4. washwas washed with methanol
  5. customThe organic solvent in the filtrate was removed under reduced pressure
  6. additionThe reaction mixture was diluted by 200 mL DCM
  7. extractionThe mixture was extracted twice by DCM
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. filtrationAfter filtration and concentration
  10. customthe resulting residue was purified via silica gel FCC (Methanol/DCM=0 to 10%)

출처 및 근거

ORD 기록
ord-c4006967662e4ae88443d67174768e47
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846656B2

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