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

HRID 63897ノート

反応式

HRID 63897 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7953b887094941508f48dae4311607fe
出典データセット
uspto-grants-2016_09
特許番号
US09447114B2

反応ノート

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