Dimethyl Sulfoxide → 2-(2-Methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-3-yl)acetaldehyde

HRID 1271535ノート

反応式

HRID 1271535 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH2:13][C:14]1[C:19](=[O:20])[N:18]2[CH2:21][CH2:22][CH2:23][CH2:24][C:17]2=[N:16][C:15]=1[CH3:25].C(N(CC)CC)C>C(Cl)Cl.O>[CH3:25][C:15]1[N:16]=[C:17]2[CH2:24][CH2:23][CH2:22][CH2:21][N:18]2[C:19](=[O:20])[C:14]=1[CH2:13][CH:12]=[O:11]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 114131273-(2-hydroxyethyl)-2-methyl-4H,6H,7H,8H,9H-pyrido(1,2-a)pyrimidin-4-one

生成物 1

HCID 102144672-(2-Methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-3-yl)acetaldehyde収率 99%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred mixture of 2.2 mL (25.22 mmoles) of oxalyl chloride in 70 mL of anhydrous methylene chloride at low temperature (−70° C. to −50° C.) and under inert atmosphere, 4.1 mL (57.78 mmoles) of dimethyl sulfoxide were added. Then, a solution of 5 g (24.02 mmoles) of 3-(2-hydroxyethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (X) in 30 mL of methylene chloride was added. After 30 minutes, 14.6 mL (104.75 mmoles) of triethylamine were added and the mixture was warmed for 45 minutes at room temperature. 75 mL of water were poured and the organic phase was decanted. The aqueous phase was removed with methylene chloride. All the organic phases were dried over anhydrous sodium sulphate, filtered and the solvent was evaporated to give 4.90 g (99%) of (2-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-3-yl)-acetaldehyde (II) as an oily residue. The compound thus obtained was pure enough as to be used in the subsequent reaction step with no prior purification.

後処理

  1. customthe organic phase was decanted
  2. customThe aqueous phase was removed with methylene chloride
  3. dry with materialAll the organic phases were dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-c54837a1539643eb839addf070408abf
出典データセット
uspto-grants-2007_04
特許番号
US07205405B2

反応ノート

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