Ethyl Acetate → tert-butyl ((1S,3R)-3-((2-chloro-4-methoxypyrimidin-5-yl)ethynyl)cyclohexyl)carbamate

HRID 2284787ノート

反応式

HRID 2284787 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5](I)=[CH:4][N:3]=1.[C:11]([C@@H:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:14]1)#[CH:12].C(OCC)(=O)C.[Cl-].[NH4+]>CN(C)C=O.C(N(CC)CC)C.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.[Cu]I>[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:12]#[C:11][C@@H:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:14]2)=[CH:4][N:3]=1

参加物

9

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 151888882-Chloro-5-iodo-4-methoxypyrimidineHCID 90051794tert-butyl ((1S,3R)-3-ethynylcyclohexyl)carbamate

生成物 1

HCID 117861333tert-butyl ((1S,3R)-3-((2-chloro-4-methoxypyrimidin-5-yl)ethynyl)cyclohexyl)carbamate収率 86.4%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of 2-chloro-5-iodo-4-methoxypyrimidine (Q1, 101 mg), tert-butyl ((1S,3R)-3-ethynylcyclohexyl)carbamate (P0, 100 mg), bis(triphenylphosphine)palladium(II) dichloride (26 mg) and copper(I) iodide (14 mg) in N,N-dimethylformamide (3 mL), triethylamine (258 μL) was added at room temperature, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture, ethyl acetate and saturated aqueous ammonium chloride were added. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 88 to 50% hexane in ethyl acetate) to obtain tert-butyl ((1S,3R)-3-((2-chloro-4-methoxypyrimidin-5-yl)ethynyl)cyclohexyl)carbamate (Q2, 118 mg).

後処理

  1. customThe organic layer was separated
  2. washwashed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 88 to 50% hexane in ethyl acetate)

出典と根拠

ORDレコード
ord-2969d906fae1443cbb5b8aeee917db53
出典データセット
uspto-grants-2015_09
特許番号
US09145415B2

反応ノート

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