Tetrahydrofuran → Isohexane ethyl acetate

HRID 723432

반응식

HRID 723432 반응식
[O:1]1C=CN=C1.[Li]CCCC.ClC1C2N=NN([CH2:22][C:23]3[CH:28]=C[CH:26]=[CH:25][C:24]=3F)C=2N=C(N)N=1.[CH2:30]1[CH2:34][O:33][CH2:32][CH2:31]1>[Cl-].[Cl-].[Zn+2].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>[CH3:26][CH2:25][CH2:24][CH:23]([CH3:28])[CH3:22].[CH3:31][CH2:32][O:33][C:34]([CH3:30])=[O:1]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 9255OxazoleHCID 218745675-amino-7-chloro-3-(2-fluorobenzyl)-3H-1,2,3-triazolo[4,5-d]pyrimidineHCID 178418339Butyllithium

생성물 1

HCID 21882781Isohexane ethyl acetate

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 178418397HCID 178418397, 화합물촉매

실험 절차

A stirred solution of oxazole (138 mg, 2.0 mmol) in dry THF (10 mL) at −78° C., under argon was treated with n-BuLi (1.25 mL, 1.6-M in hexanes, 2.0 mmol), stirred for 30 min, treated with a solution of ZnCl2 (2.0 mL, 1-M in Et2O, 2.0 mmol)) and allowed to warm gradually to room temperature. The mixture was treated with 7-chloro-3-(2-fluorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (280 mg, 1.0 mmol) and Pd(PPh3)4 (100 mg), refluxed for 4 h and partitioned between saturated NH4Cl solution (10 mL) and EtOAc (10 mL). The organic phase was dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; iso-hexane:EtOAc (1:1), then neat EtOAc] to give the title compound (6 mg, 2%) as a beige solid.

후처리

  1. temperaturerefluxed for 4 h
  2. custompartitioned between saturated NH4Cl solution (10 mL) and EtOAc (10 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography [SiO2

출처 및 근거

ORD 기록
ord-2e45175e60c346a9a38a2d4ef9da3763
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141575B2

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