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Triphenylarsine → (2S)-N2-[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]-4-methyl-pentane-1,2-diamine

HRID 72786
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HRID 72786 반응식
Br[C:2]1[C:3]([NH:9][C@@H:10]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:11][NH:12]C(=O)OC(C)(C)C)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH2:24]([O:26][CH:27]([O:30][CH2:31][CH3:32])[C:28]#[CH:29])[CH3:25].C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C(N(CC)CC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:8][C:5]1[N:4]=[C:3]([NH:9][C@@H:10]([CH2:20][CH:21]([CH3:22])[CH3:23])[CH2:11][NH2:12])[C:2]([C:29]#[C:28][CH:27]([O:30][CH2:31][CH3:32])[O:26][CH2:24][CH3:25])=[CH:7][N:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 11773TriphenylarsineHCID 662853,3-DiethoxypropyneHCID 86695597tert-butyl N-[(2S)-2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]-4-methyl-pentyl]carbamate

생성물 1

HCID 86695596(2S)-N2-[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]-4-methyl-pentane-1,2-diamine

시약·촉매·용매 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 1140Toluene용매
HCID 8471Triethylamine용매

실험 절차

To a solution of tert-butyl N-[(2S)-2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]-4-methyl-pentyl]carbamate 5.0 g (12.3 mmole) in toluene (36 mL) and triethyl amine (7.2 mL) was added under nitrogen, 3,3-diethoxyprop-1-yne 2.8 mL (19.7 mmole), Pd2(dba)3 1.1 g (1.23 mmole), and triphenylarsine 3.8 g (12.3 mmole). The contents were heated to 70 degrees for 24 hrs. After cooling to room temperature, the reaction mixture was filtered through CELITE™ and then concentrated under vacuum. The crude product was columned over silica gel using hexane/ethyl acetate (0-30%) to afford (2S)—N2-[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]-4-methyl-pentane-1,2-diamine. LCMS (ESI) 455 (M+H).

후처리

  1. temperatureThe contents were heated to 70 degrees for 24 hrs
  2. filtrationthe reaction mixture was filtered through CELITE™
  3. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-59c3c39d263c4e4c975b19f4d07361a6
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08829012B2

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