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2,4-Dimethoxy-3-iodopyrimidine → (s)-n-Methyl-n-(tert-butoxycarbonyl)-5-(2,4-dimethoxy-5-pyrimidinyl)-4-penten-2-amine

HRID 489738
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인쇄 미리보기

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HRID 489738 반응식
CN[C@H](CC=CC1C(O)=NC(O)=NC=1)C.[CH3:16][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:18]([CH2:20][CH:21]=[CH2:22])[CH3:19].[CH3:30][O:31][CH:32]1[N:37](I)[C:36]([O:39][CH3:40])=[CH:35][CH:34]=[N:33]1>[Pd]>[CH3:16][N:17]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[C@H:18]([CH2:20][CH:21]=[CH:22][C:35]1[C:36]([O:39][CH3:40])=[N:37][C:32]([O:31][CH3:30])=[N:33][CH:34]=1)[CH3:19]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 221444912,4-Dimethoxy-3-iodopyrimidineHCID 54671306(S)-tert-butyl methyl(pent-4-en-2-yl)carbamateHCID 178484883HCID 178484883, 화합물

생성물 1

HCID 68597348(s)-n-Methyl-n-(tert-butoxycarbonyl)-5-(2,4-dimethoxy-5-pyrimidinyl)-4-penten-2-amine

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

Scheme I shows the synthesis of (S)-N-methyl-5-(2,4-dihydroxy-5-pyrimidinyl)-4-penten-2-amine. In this synthesis, the previously described (S)-N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine is subjected to Heck-type coupling conditions by reaction with a 2,4-dimethoxy-3-iodopyrimidine in the presence of a palladium catalyst to form (S)-N-methyl-N-(tert-butoxycarbonyl)-5-(2,4-dimethoxy-5-pyrimidinyl)-4-penten-2-amine. The methoxy groups can be converted to hydroxy groups, concurrent with the cleavage of the amine protecting group, by reaction with trimethylsilyl iodide in methanol/dichloromethane to yield the desired N-methyl-5-(2,4-dihydroxy-5-pyrimidinyl)-4-penten-2-amine compound as a hydroiodide salt. Alternately, the tert-butoxycarbonyl protecting group can be selectively removed by trifluoroacetic acid, as described previously, to give the (S)-N-methyl-5-(2,4-dimethoxy-5-pyrimidinyl)-4-penten-2-amine. Cleavage of the methyl ethers using 48% HBr then provides (S)-N-methyl-5-(2,4-dihydroxy-5-pyrimidinyl)-4-penten-2-amine.

후처리

  1. customIn this synthesis

출처 및 근거

ORD 기록
ord-17a5aca192454e56b64e6c23deb3ab2b
출처 데이터셋
uspto-grants-2005_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06979695B2

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