Potassium Hydroxide → N-(2-Fluoro-4-iodo-phenyl)-2-pyrimidin-4-ylmethyl-malonamic acid ethyl ester

HRID 450114ノート

反応式

HRID 450114 の反応式
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[F:16])=[O:7])[CH3:2].Cl[CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][N:21]=1.[OH-].[K+]>>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][N:21]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[F:16])=[O:7])[CH3:2]

参加物

4

反応物 3

HCID 14797Potassium HydroxideHCID 131235534-(Chloromethyl)pyrimidineHCID 67234460N-(2-Fluoro-4-iodo-phenyl)-malonamic acid ethyl ester

生成物 1

HCID 67234244N-(2-Fluoro-4-iodo-phenyl)-2-pyrimidin-4-ylmethyl-malonamic acid ethyl ester収率 40%

実験手順

N-(2-Fluoro-4-iodo-phenyl)-malonamic acid ethyl ester (20.5 g, 58.4 mmol), 4-chloromethyl-pyrimidine (5.0 g, 38.9 mmol) and potassium hydroxide (3.28 g, 58.4 mmol) were dissolved in IMS (200 mL). The reaction mixture was stirred at room temperature for 16 hours then concentrated in vacuo. The resultant residue was dissolved in ethyl acetate (30 mL), washed with water (20 mL) and the aqueous fraction extracted twice with ethyl acetate (2×10 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 10-40% ethyl acetate in cyclohexane) to yield the title compound as an off-white solid (6.9 g, 39%). LCMS (Method B): RT=3.29 min, M+H+=444.

後処理

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe resultant residue was dissolved in ethyl acetate (30 mL)
  3. washwashed with water (20 mL)
  4. extractionthe aqueous fraction extracted twice with ethyl acetate (2×10 mL)
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c7e31450bb88434181654ae2ffe64e7d
出典データセット
uspto-grants-2013_07
特許番号
US08486963B2

反応ノート

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