7-chloro-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one → 2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one

HRID 538223ノート

反応式

HRID 538223 の反応式
Cl[C:2]1[NH:7][C:6](=[O:8])[N:5]2[CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:4]2[CH:3]=1>CCOC(C)=O.CO.[OH-].[Pd+2].[OH-]>[O:13]([CH2:12][C:10]1[N:11]=[C:4]2[CH:3]=[CH:2][NH:7][C:6](=[O:8])[N:5]2[CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

5

反応物 1

HCID 1363786247-chloro-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one

生成物 1

HCID 1360357622-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one収率 92.7%

試薬・触媒・溶媒 3

HCID 9942167Palladium hydroxide触媒3 回HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

10% Palladium hydroxide (0.43 g, 3 mmol) was added to a solution of 7-chloro-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (0.24 g, 0.85 mmol) and TEA (0.6 mL, 4.32 mmol) in a mixture of AcOEt and MeOH (60 mL). The mixture was hydrogenated in a Parr reactor (45 psi) at 50° C. for 16 hours. Then 10% palladium hydroxide (0.18 g, 0.43 mmol) was added and the mixture hydrogenated again in a Parr reactor (45 psi) at 50° C. for 16 hours. The mixture was hydrogenated over 5 cycles with addition of 10% palladium hydroxide (0.18 g, 0.43 mmol) every cycle. The mixture was filtered through a pad of diatomaceous earth and washed with MeOH. The solvents were evaporated in vacuo and the crude product purified by flash column chromatography (silica; 7 M solution of ammonia in MeOH in DCM with a gradient of 0/100 to 40/60). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (0.19 g, 92% yield) as a white solid.

後処理

  1. waitthe mixture hydrogenated again in a Parr reactor (45 psi) at 50° C. for 16 hours
  2. filtrationThe mixture was filtered through a pad of diatomaceous earth
  3. washwashed with MeOH
  4. customThe solvents were evaporated in vacuo
  5. customthe crude product purified by flash column chromatography (silica
  6. customThe desired fractions were collected
  7. customthe solvents evaporated in vacuo

出典と根拠

ORDレコード
ord-6821acc5ca40471cac39aef63718834c
出典データセット
uspto-grants-2014_10
特許番号
US08865725B2

反応ノート

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