Potassium Phosphate, Tribasic → 4-(Pyrimidin-5-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 547917

反応式

HRID 547917 の反応式
Br[C:2]1[CH:3]=[N:4][C:5](C2C=CC=CC=2)=[N:6][CH:7]=1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(N(CC)C(=O)C1C(=CC=CC=1)O)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu]I>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([NH:27][C:2]2[CH:7]=[N:6][CH:5]=[N:4][CH:3]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 88006DiethylsalicylamideHCID 12682914-Amino-1-Boc-piperidineHCID 143877455-Bromo-2-phenylpyrimidine

生成物 1

HCID 671982114-(Pyrimidin-5-ylamino)-piperidine-1-carboxylic acid tert-butyl ester収率 47.8%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 5-bromo-2-phenyl-pyrimidine (3.50 g, 14.89 mmol, 1.0 equiv), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (4.48 g, 22.33 mmol, 1.5 equiv), copper(I) iodide (0.28 g, 1.49 mmol, 0.1 equiv), N,N-diethylsalicylamide (0.58 g, 2.98 mmol, 0.2 equiv) and K3PO4 (3.16 g, 14.89 mmol, 1.0 equiv) in degassed DMF (30 mL) was heated under Ar to 90° C. for 24 h. The solvent was removed under reduced pressure and the crude reaction product extracted from water (300 mL) and 25% NH4OH (30 mL) with ethyl acetate (3×300 mL). The combined organic phases were dried over Na2SO4, concentrated by evaporation under reduced pressure and the crude material purified by silica column chromatography eluting with a gradient of heptane/ethyl acetate (4:1→1:1) to provide 1.98 g (38%) of the title compound. MS (ESI): 377.1 [M+Na]+.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe crude reaction product
  3. extractionextracted from water (300 mL) and 25% NH4OH (30 mL) with ethyl acetate (3×300 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customthe crude material purified by silica column chromatography
  7. washeluting with a gradient of heptane/ethyl acetate (4:1→1:1)

出典と根拠

ORDレコード
ord-2a7eace60b054b44a3243b176692773e
出典データセット
uspto-grants-2011_05
特許番号
US07939661B2

関連ノート

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