Diethyl Ether → Tert-butyl 2-(3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)acetate

HRID 219265노트

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HRID 219265 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([CH3:12])[C:5]2=[O:13].[Cl-].[C:15]([O:19][C:20](=[O:23])[CH2:21][Zn+])([CH3:18])([CH3:17])[CH3:16].C(OCC)C>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(P(C(C)(C)C)[C-]1C=CC=C1)(C)C.C1C=CC([C-]2C(C3C=CC=CC=3)=C(C3C=CC=CC=3)C(C3C=CC=CC=3)=C2C2C=CC=CC=2)=CC=1.[Fe+2]>[CH3:12][N:6]1[C:5](=[O:13])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH2:21][C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:23])[CH:3]=2)[N:8]=[CH:7]1

참가 물질

7

반응물 3

HCID 3283Diethyl EtherHCID 42169776-Bromo-3-methyl-3,4-dihydroquinazolin-4-oneHCID 178451183HCID 178451183, 화합물

생성물 1

HCID 57690984Tert-butyl 2-(3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)acetate

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 129828017Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene촉매HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

To a solution of 6-bromo-3-methylquinazolin-4(3H)-one (0.485 g, 2.0 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.19 g, 0.20 mmol) and Q-phos (0.20 g) in 40 mL of THF was added 2-tert-butoxy-2-oxoethylzinc chloride 0.5 M in diethyl ether (8.1 ml, 4.1 mmol). The reaction was heated at 50° C. for 16 hours and was quenched with 40 mL of satd. NH4Cl. The mixture was diluted with 60 mL of EtOAc. The organic phase was separated, washed with brine, dried over Na2SO4 and concentrated in vacuo to give red solid. The residue was purified by a silica gel column chromatography (5% EtOAc/Hex to EtOAC) to provide a red solid. MS (ESI pos. ion) m/z: 275 (MH+). Calc'd exact mass for C15H18N2O3: 274.

후처리

  1. customwas quenched with 40 mL of satd
  2. additionThe mixture was diluted with 60 mL of EtOAc
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto give red solid
  8. customThe residue was purified by a silica gel column chromatography (5% EtOAc/Hex to EtOAC)
  9. customto provide a red solid

출처 및 근거

ORD 기록
ord-adc4f2dfe3fe4a29b4481d89d5aacbb5
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198448B2

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