Diethyl Ether → 2,2-dimethylpropionic Acid 4-(dimethylamino-methyleneamino)-5-fluoro-pyrimidin-2-yloxymethyl Ester

HRID 705588ノート

反応式

HRID 705588 の反応式
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:20]([O:26][CH2:27]Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].C(OCC)C>CN(C=O)C>[CH3:12][N:11]([CH:10]=[N:9][C:3]1[C:2]([F:1])=[CH:7][N:6]=[C:5]([O:8][CH2:27][O:26][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[N:4]=1)[CH3:13]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 87885Chloromethyl pivalateHCID 178484257HCID 178484257、化合物

生成物 1

HCID 578184502,2-dimethylpropionic Acid 4-(dimethylamino-methyleneamino)-5-fluoro-pyrimidin-2-yloxymethyl Ester収率 9.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N′-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (100 mg, 0.54 mmol), cesium carbonate (196 mg, 0.60 mmol), and chloromethyl pivalate (90 mg, 0.6 mmol) were shaken together in DMF (3 mL) at ambient temperature for 16 hours. The reaction mixture was partitioned between ethyl acetate and water, dried over magnesium sulfate, filtered and evaporated to yield a colorless oil which was treated with diethyl ether (3-4 mL) to produce a solid. The solid was removed and the ether solution was placed onto a silica gel column and eluted with ethyl acetate in petroleum ether (0-50% gradient) to isolate 14 mg, 0.05 mmol (9%) of the title compound as a white solid: mp 86-88° C.; 1H NMR (CDCl3) δ 8.73 (s, 1H), 8.06 (d, J=2.6 Hz, 1H), 6.04 (s, 2H), 3.20 (s, 3H), 3.18 (s, 3H), 1.16 (s, 9H); HPLC-MS (ESI) m/z 299 (M+H)+.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto yield a colorless oil which
  6. customto produce a solid
  7. customThe solid was removed
  8. washeluted with ethyl acetate in petroleum ether (0-50% gradient)

出典と根拠

ORDレコード
ord-8f9c41c5f4e7400190e99ec9b36c7cef
出典データセット
uspto-grants-2015_11
特許番号
US09174970B2

反応ノート

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