Benzeneethanamine, alpha-methyl-, phosphate (1:1) → (R)-7'-(3,6-dihydro-2H-pyran-4-yl)-3'-fluoro-2'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 335744

反応式

C([Sn](CCCC)(CCCC)[C:6]1[CH:7]=[N:8][CH:9]=[N:10][CH:11]=1)CCC.CC(N)CC1C=CC=CC=1.OP(O)(O)=O.FC(F)(F)S(O[C:41]1[CH:54]=[C:53]2[C:44]([O:45][C:46]3[CH:47]=[CH:48][C:49]([C:60]4[CH2:61][CH2:62][O:63][CH2:64][CH:65]=4)=[CH:50][C:51]=3[C@@:52]32[CH2:58][O:57][C:56]([NH2:59])=[N:55]3)=[CH:43][C:42]=1[F:66])(=O)=O>CN(C=O)C>[O:63]1[CH2:64][CH:65]=[C:60]([C:49]2[CH:50]=[C:51]3[C:46]([O:45][C:44]4[CH:43]=[C:42]([F:66])[C:41]([C:6]5[CH:11]=[N:10][CH:9]=[N:8][CH:7]=5)=[CH:54][C:53]=4[C@:52]43[CH2:58][O:57][C:56]([NH2:59])=[N:55]4)=[CH:47][CH:48]=2)[CH2:61][CH2:62]1

参加物

反応条件

温度: 130 °C

実験手順

A mixture of 5-(tributylstannyl)pyrimidine (73.8 mg, 0.200 mmol), AmPhos (4.24 mg, 5.99 μmol) and (R)-2-amino-2′-(3,6-dihydro-2H-pyran-4-yl)-6′-fluoro-5H-spiro[oxazole-4,9′-xanthene]-7′-yl trifluoromethanesulfonate (50 mg, 0.100 mmol) in 0.3 mL of DMF was heated at 130° C. for 1 hour. After cooling and evaporation of the solvent under high vacuum, the mixture was purified by silica gel chromatography (DCM to DCM/EA=1:1 to 1:2 to pure EA to EA/MeOH=100:5 to 100:10) to provide (R)-7′-(3,6-dihydro-2H-pyran-4-yl)-3′-fluoro-2′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as an off-white solid.

後処理

temperatureAfter cooling
customevaporation of the solvent under high vacuum
customthe mixture was purified by silica gel chromatography (DCM to DCM/EA=1:1 to 1:2 to pure EA to EA/MeOH=100:5 to 100:10)

出典と根拠

ORDレコード: ord-83c10385655c4916ac2733575dba14e4
出典データセット: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08883782B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

関連ノート