Triethylamine → (5-Bromo-2-chloro-pyrimidin-4-yl)-(2-methoxy-1,1-dimethyl-ethyl)-amine

HRID 82280

반응식

HRID 82280 반응식
C(N(CC)CC)C.[Br:8][C:9]1[C:10](Cl)=[N:11][C:12]([Cl:15])=[N:13][CH:14]=1.[CH3:17][O:18][CH2:19][C:20]([NH2:23])([CH3:22])[CH3:21].N1C=CC=NC=1>C(#N)C>[Br:8][C:9]1[C:10]([NH:23][C:20]([CH3:22])([CH3:21])[CH2:19][O:18][CH3:17])=[N:11][C:12]([Cl:15])=[N:13][CH:14]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 9260PyrimidineHCID 886661-Methoxy-2-methylpropan-2-amineHCID 2899735-Bromo-2,4-dichloropyrimidine

생성물 1

HCID 86672124(5-Bromo-2-chloro-pyrimidin-4-yl)-(2-methoxy-1,1-dimethyl-ethyl)-amine수율 23%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Triethyl amine (73.1 mL, 526.6 mmol) was added slowly to a solution of 5-Bromo-2,4-dichloro-pyrimidine (40 g, 175.5 mmol) in acetonitrile (400 mL) at 00° C. and then 2-Methoxy-1,1-dimethyl-ethylamine (Preparation 255, 23.4 g, 263.3 mmol) was added to the mixture portion wise. The reaction mixture was stirred for another 16 hours at room temperature. TLC showed the presence of unreacted starting pyrimidine, but the reaction was not continued further. All the volatiles were removed in vacuo and the residue was taken in ethyl acetate, washed with water, brine, dried over sodium sulphate and evaporated to dryness in vacuo. The crude material was purified by column chromatography on silica gel (100-200 mesh, gradient of ethyl acetate:hexane 1:9 to 2:4) to afford the title compound as white solid in 23% yield (10 g of starting pyrimidine was recovered), 12 g.

후처리

  1. customAll the volatiles were removed in vacuo
  2. washwashed with water, brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated to dryness in vacuo
  5. customThe crude material was purified by column chromatography on silica gel (100-200 mesh, gradient of ethyl acetate:hexane 1:9 to 2:4)

출처 및 근거

ORD 기록
ord-b8b92e1d45b34c79bf8e55407ea18755
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

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