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

HRID 547917

반응식

HRID 547917 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-2a7eace60b054b44a3243b176692773e
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939661B2

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