Sodium Carbonate → (R)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)phenol

HRID 521363ノート

反応式

HRID 521363 の反応式
Cl[C:2]1[C:3]2[C@H:10]([CH3:11])[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C.O.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:11][C@H:10]1[C:3]2[C:2]([C:16]3[CH:17]=[CH:18][C:13]([OH:12])=[CH:14][CH:15]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH2:8][CH2:9]1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 59670769(R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine

生成物 1

HCID 136385952(R)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)phenol収率 87.1%

試薬・触媒・溶媒 4

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒2 回HCID 3776Isopropanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

(R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (137 mg, 0.812 mmol) and 4-hydroxybenzeneboronic acid (123 mg, 0.894 mmol) was dissolved in isopropyl alcohol (1.6 mL). Sodium carbonate in water (0.97 mL, 1.0M) was added slowly, followed by bis(triphenylphosphine)palladium chloride (26.5 mg, 0.0378 mmol). The mixture was stirred at 100° C. (bath) for 16 hours. The contents were diluted with water (5 mL) and EtOAc (10 mL). The aqueous layer was separated and extracted with EtOAc (2×5 mL). The combined EtOAc solutions were washed with brine (5 mL) and dried (Na2SO4). The crude was purified by flash chromatography to give (R)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)phenol (160 mg, 87%) as viscous oil which solidified upon standing.

後処理

  1. customThe aqueous layer was separated
  2. extractionextracted with EtOAc (2×5 mL)
  3. washThe combined EtOAc solutions were washed with brine (5 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe crude was purified by flash chromatography

出典と根拠

ORDレコード
ord-5f1bc0142e7e43e796508b46dfc8963c
出典データセット
uspto-grants-2016_05
特許番号
US09328091B2

反応ノート

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