Potassium Phosphate, Tribasic → 6-(3,4-dichlorophenyl)-3-(3-hydroxypropyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 63897

반응식

HRID 63897 반응식
Br[C:2]1[S:17][C:5]2[N:6]([CH3:16])[C:7](=[O:15])[N:8]([CH2:11][CH2:12][CH2:13][OH:14])[C:9](=[O:10])[C:4]=2[C:3]=1[CH3:18].[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][C:25]=1[Cl:26].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CC(=O)OCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:19][C:20]1[CH:21]=[C:22]([C:2]2[S:17][C:5]3[N:6]([CH3:16])[C:7](=[O:15])[N:8]([CH2:11][CH2:12][CH2:13][OH:14])[C:9](=[O:10])[C:4]=3[C:3]=2[CH3:18])[CH:23]=[CH:24][C:25]=1[Cl:26]

참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 27343303,4-Dichlorobenzeneboronic acidHCID 1188631236-bromo-3-(3-hydroxypropyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

생성물 1

HCID 1188630956-(3,4-dichlorophenyl)-3-(3-hydroxypropyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione수율 27.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
85 °C

실험 절차

To a solution of 6-bromo-3-(3-hydroxypropyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (50 mg, 0.15 mmol) in dioxane (2 mL) was added 3,4-dichlorophenylboronic acid (57.3 mg, 0.3 mmol), Pd(PPh3)4 (17.3 mg, 0.015 mmol) and aq. 2M K3PO4 (0.4 mL). The reaction was heated at 85° C. for 1 h, cooled to RT then diluted with EA (20 mL). The organic layer was washed with brine (20 mL) and aq. NH4Cl (20 mL), dried with Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 6-(3,4-dichlorophenyl)-3-(3-hydroxypropyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (15.0 mg, 27.4% yield) as a white solid. 1H NMR (CDCl3) δ: 7.55-7.48 (m, 2H), 7.24 (d, J=2.1 Hz, 1H), 4.27-4.14 (m, 2H), 3.60-3.50 (m, 5H), 3.27 (t, J=6.5 Hz, 1H), 2.54 (s, 3H), 2.00-1.85 (m, 2H). LCMS: MH+ 399 and TR=3.000 min.

후처리

  1. temperaturecooled to RT
  2. washThe organic layer was washed with brine (20 mL) and aq. NH4Cl (20 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated to a residue which
  5. customwas purified by Prep HPLC

출처 및 근거

ORD 기록
ord-7953b887094941508f48dae4311607fe
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447114B2

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