Sodium Carbonate → (S)-4-(5-(3-fluoro-4-(2-morpholinoethoxy)phenyl)pyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine

HRID 1478573ノート

反応式

HRID 1478573 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][N:15]3[C:19]4=[N:20][C:21]([C:24]5[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=5)=[CH:22][N:23]=[C:18]4[N:17]=[N:16]3)[CH2:9]2)=[N:6][CH:7]=1.[F:30][C:31]1[CH:45]=[C:44](B2OC(C)(C)C(C)(C)O2)[CH:43]=[CH:42][C:32]=1[O:33][CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:30][C:31]1[CH:45]=[C:44]([C:2]2[CH:3]=[N:4][C:5]([N:8]3[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][N:15]4[C:19]5=[N:20][C:21]([C:24]6[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=6)=[CH:22][N:23]=[C:18]5[N:17]=[N:16]4)[CH2:9]3)=[N:6][CH:7]=2)[CH:43]=[CH:42][C:32]=1[O:33][CH2:34][CH2:35][N:36]1[CH2:37][CH2:38][O:39][CH2:40][CH2:41]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 73507291HCID 73507291、化合物HCID 1317365094-(2-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenoxy)ethyl)morpholine

生成物 1

HCID 118364799(S)-4-(5-(3-fluoro-4-(2-morpholinoethoxy)phenyl)pyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine収率 40%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
105 °C

実験手順

(S)-4-(5-bromopyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine 15 mg (0.033 mmol) was dissolved in dioxane 1 ml, and 4-(2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenoxy)ethyl)morpholine 17 mg (0.049 mmol) and 1M sodium carbonate 98.4 ul (0.098 mmol) were added. Pd(PPh3)4 2 mg (0.0016 mmol) was added, and the mixture was purged with N2 (g), followed by stirring at 105° C. for 4 hours. When the reaction was completed, the reaction mixture was extracted with ethyl acetate and brine, and the organic layer was dried over Na2SO4. Prep LC with 4% MeOH/MC gave a product 7.8 mg (40%).

後処理

  1. customthe mixture was purged with N2 (g)
  2. extractionthe reaction mixture was extracted with ethyl acetate and brine
  3. dry with materialthe organic layer was dried over Na2SO4

出典と根拠

ORDレコード
ord-222052855fbb4c2b9030509a599630f6
出典データセット
uspto-grants-2016_08
特許番号
US09403831B2

反応ノート

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