Sodium Carbonate → HCID 71282814、化合物

HRID 1752433ノート

反応式

HRID 1752433 の反応式
[F:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10](B3OC(C)(C)C(C)(C)O3)=[CH:9][N:8]=2)=[CH:4][CH:3]=1.[NH2:24][C:25](=[O:39])[C@@H:26]([NH:28][C:29]1[N:34]=[C:33](Cl)[N:32]=[C:31]([C:36]([NH2:38])=[O:37])[CH:30]=1)[CH3:27].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:24][C:25](=[O:39])[C@@H:26]([NH:28][C:29]1[N:34]=[C:33]([C:10]2[CH:9]=[N:8][C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:23][CH:22]=3)=[CH:12][CH:11]=2)[N:32]=[C:31]([C:36]([NH2:38])=[O:37])[CH:30]=1)[CH3:27]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 71092939HCID 71092939、化合物HCID 89422280HCID 89422280、化合物

生成物 1

HCID 71282814HCID 71282814、化合物収率 50.5%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 86587095Dimethoxyethane ethanol water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-(4-fluorophenoxy)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (158 mg, 0.5 mmol), (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-chloropyrimidine-4-carboxamide (121 mg, 0.5 mmol), Na2CO3 (2 M, 1 mL, 2 mmol) and Pd(PPh3)2Cl2 (20 mg, 0.025 mmol) in DME/EtOH/H2O (2 mL/1 mL/2 mL) was purged with Ar for one minute, then stirred at 100° C. for 14 hrs. The reaction mixture was then worked up with DCM. The DCM was isolated, dried over MgSO4, and removed under vacuum. The residue was subjected to silica gel flash chromatography using dichloromethane/methanol as the eluent to give (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(6-(4-fluorophenoxy)pyridin-3-yl)pyrimidine-4-carboxamide as a gray solid (100 mg, yield 50%). NMR (DMSO-d6): 9.3 (1H, s), 8.9 (1H, m), 8.3 (1H, s), 8.05 (1H, m), 7.75 (1H, s), 7.5 (1H, s), 7.2-7.4 (4H, m), 6.95-7.15 (2H, m), 6.80 (1H, s), 4.5 (1H, m), 1.35 (3H, d, J=7.0 Hz). LC/MS: m/z=398 [M+H]+.

後処理

  1. customwas purged with Ar for one minute
  2. customThe DCM was isolated
  3. dry with materialdried over MgSO4
  4. customremoved under vacuum

出典と根拠

ORDレコード
ord-81fb9a18293b40be9f59adeaa28f05f4
出典データセット
uspto-grants-2015_10
特許番号
US09163008B2

反応ノート

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