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Potassium Phosphate, Tribasic → 5-fluoro-3-(4-(methylthio)pyrimidin-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine

HRID 2171900
ノート
印刷プレビュー

反応式

HRID 2171900 の反応式
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:18][C:19]1[CH:20]=[C:21]2[C:27](B3OC(C)(C)C(C)(C)O3)=[N:26][N:25]([C:37]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:22]2=[N:23][CH:24]=1>O.CC1CCCO1.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]>[F:18][C:19]1[CH:20]=[C:21]2[C:27]([C:2]3[N:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][N:3]=3)=[N:26][N:25]([C:37]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:22]2=[N:23][CH:24]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 164271482-Chloro-4-(methylthio)pyrimidineHCID 679757175-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine2 回

生成物 1

HCID 712479685-fluoro-3-(4-(methylthio)pyrimidin-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine

試薬・触媒・溶媒 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 962Water溶媒
HCID 73012-Methyltetrahydrofuran溶媒

反応条件

温度
95 °C

実験手順

A solution of 2-chloro-4-methylsulfanyl-pyrimidine (0.25 g, 1.56 mmol), K3PO4 (0.99 g, 4.67 mmol) and 5-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine, 135a, (0.87 g, 1.71 mmol) in water (1 mL) and 2-methyltetrahydrofuran (9 mL) was degassed under a stream of nitrogen for 15 minutes. Then, Pd2(dba)3 (0.04 g, 0.05 mmol) was added and the mixture was degassed for an additional 2-3 minutes. The vessel was sealed and heated to 95° C. overnight. After separating the layers, the organic phase was washed with water. The resulting solid was filtered and washed with ether and MeTHF. Filtered through PSA cartridge with MeOH/dichloromethane mixture to give the desired product as a white solid: LCMS Gradient 60-98%, 0.1% formic acid, 7 min, C4/ACN, Retention Time=2.68 min (M+Na) 526.1.

後処理

  1. customthe mixture was degassed for an additional 2-3 minutes
  2. customThe vessel was sealed
  3. customAfter separating the layers
  4. washthe organic phase was washed with water
  5. filtrationThe resulting solid was filtered
  6. washwashed with ether and MeTHF
  7. filtrationFiltered through PSA cartridge with MeOH/dichloromethane mixture

出典と根拠

ORDレコード
ord-5f432812757b4d90aa90fe7ae1da9e10
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09051319B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート