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N,N,N',N'-Tetramethyl-1,3-diaminopropane → 2-Amino-5-(4-(3-(tert-butyldimethylsilyloxy)propoxy)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

HRID 2207090
ノート
印刷プレビュー

反応式

HRID 2207090 の反応式
[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9](Cl)(=[O:11])=[O:10].CN(C)CCCN(C)C.[NH2:23][C:24]1[N:29]=[C:28]([OH:30])[C:27]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])=[CH:34][C:33]=2[O:50][CH3:51])=[C:26]([CH3:52])[N:25]=1>C1COCC1.O>[CH3:13][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:30][C:28]1[C:27]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][O:42][Si:43]([C:46]([CH3:49])([CH3:47])[CH3:48])([CH3:44])[CH3:45])=[CH:34][C:33]=2[O:50][CH3:51])=[C:26]([CH3:52])[N:25]=[C:24]([NH2:23])[N:29]=1)(=[O:11])=[O:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8084N,N,N',N'-Tetramethyl-1,3-diaminopropaneHCID 130462-Mesitylenesulfonyl chlorideHCID 1784934872-amino-5-[[4-[3-[tert-butyl(dimethyl)silyl]oxypropoxy]-2-methoxyphenyl]methyl]-6-methyl-1H-pyrimidin-4-one

生成物 1

HCID 871670752-Amino-5-(4-(3-(tert-butyldimethylsilyloxy)propoxy)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate収率 95.4%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

2-Mesitylenesulfonyl chloride (4.96 g, 22.7 mmol) was added to a solution of N,N,N′,N′-tetramethyl-1,3-propanediamine (3.79 mL, 22.7 mmol) and the product of example 8 step (v) (6.55 g, 15.1 mmol) in THF (66 mL) and the mixture was stirred at RT for 3 h. The resulting mixture was diluted with water and extracted with EtOAc. And the combined organic solutions were washed with brine, dried and concentrated. The residue was purified via chromatography on silica to give 8.87 g of the subtitle compound as a white solid; 1H NMR (CDCl3); 6.93 (2H, s), 6.71 (1H, d), 6.41 (1H, d), 6.33 (1H, dd), 4.66 (2H, br s), 4.02 (2H, t), 3.78 (3H, s), 3.77-3.82 (2H, m), 3.75 (2H, s), 2.59 (6H, s), 2.31 (3H, s), 2.25 (3H, s), 1.93-2.01 (2H, m), 0.89 (9H, s), 0.05 (6H, s); LC-MS: m/z 616.

後処理

  1. extractionextracted with EtOAc
  2. washAnd the combined organic solutions were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified via chromatography on silica

出典と根拠

ORDレコード
ord-b919020b0a50457e92fec837cce461a2
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09376398B2

反応ノート

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