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

HRID 1271535노트

반응식

HRID 1271535 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c54837a1539643eb839addf070408abf
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205405B2

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