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(Diethylamino)sulfur trifluoride → 5-[2-Isopropyl-4-methoxy-5-(1-methoxy-ethyl)-phenoxy]-pyrimidine-2,4-diamine

HRID 1677290
ノート
印刷プレビュー

反応式

HRID 1677290 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][C:10]2[C:11]([CH:21]([CH3:23])[CH3:22])=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:16]([OH:18])[CH3:17])[CH:15]=2)=[CH:4][N:3]=1.[CH3:24]CN(S(F)(F)F)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:21]([C:11]1[CH:12]=[C:13]([O:19][CH3:20])[C:14]([CH:16]=[CH2:17])=[CH:15][C:10]=1[O:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1)([CH3:23])[CH3:22].[CH:21]([C:11]1[CH:12]=[C:13]([O:19][CH3:20])[C:14]([CH:16]([O:18][CH3:24])[CH3:17])=[CH:15][C:10]=1[O:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1)([CH3:23])[CH3:22]
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 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 573291161-[5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-ethanol

生成物 2

HCID 573289585-(2-Isopropyl-4-methoxy-5-vinyl-phenoxy)-pyrimidine-2,4-diamine収率 3%HCID 595986985-[2-Isopropyl-4-methoxy-5-(1-methoxy-ethyl)-phenoxy]-pyrimidine-2,4-diamine
収率 4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-[5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-ethanol (1.613 g, 5.3 mmol) in 30 ml CH2Cl2 at −78° C. was added DAST (0.935 g, 5.8 mmol). After stirring 1.5 h, saturated NaHCO3 was added and the mixture was extracted by CH2Cl2. The combined organics were washed with brine and dried Na2SO4, filtered and concentrated in vacuo. Purification via silica gel chromatography (95:5 CH2Cl2/MeOH) gave 5-(2-Isopropyl-4-methoxy-5-vinyl-phenoxy)-pyrimidine-2,4-diamine (0.044 g, 3%) as a foam ([MH]+=301) and 5-[2-Isopropyl-4-methoxy-5-(1-methoxy-ethyl)-phenoxy]-pyrimidine-2,4-diamine (0.075 g, 4%) as foam. [MH]+=303.

後処理

  1. extractionthe mixture was extracted by CH2Cl2
  2. washThe combined organics were washed with brine and dried Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification via silica gel chromatography (95:5 CH2Cl2/MeOH)

出典と根拠

ORDレコード
ord-e216b53d0b8f4b40ac5dd2d8c64aed90
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08008313B2

反応ノート

読み込み中…

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