Water → Methyl 3-hydroxy-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate

HRID 1365720노트

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HRID 1365720 반응식
CO[C:3](=[O:20])[CH2:4][C:5]1([C:16]([O:18][CH3:19])=[O:17])O[N:12]2[C:7]([C:8]([CH3:15])([CH3:14])[O:9][CH2:10][CH2:11]2)=[N:6]1.[OH2:21]>CC1C=CC(C)=CC=1C>[OH:21][C:4]1[C:3](=[O:20])[N:12]2[C:7]([C:8]([CH3:14])([CH3:15])[O:9][CH2:10][CH2:11]2)=[N:6][C:5]=1[C:16]([O:18][CH3:19])=[O:17]

참가 물질

4

반응물 2

HCID 962WaterHCID 21069965Methyl 2-(2-methoxy-2-oxoethyl)-8,8-dimethyl-2,5,6,8-tetrahydro-[1,2,4]oxadiazolo[3,2-c][1,4]oxazine-2-carboxylate

생성물 1

HCID 54708350Methyl 3-hydroxy-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate

시약·촉매·용매 1

HCID 72471,2,4-Trimethylbenzene용매

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온도
22.5 °C

실험 절차

A solution of the above crude methyl 2-(2-methoxy-2-oxoethyl)-8,8-dimethyl-2,5,6,8-tetrahydro-[1,2,4]oxadiazolo[3,2-c][1,4]oxazine-2-carboxylate (8.34 g) in 1,2,4-trimethylbenzene (80 mL) was heated at 155° C. for 9 h. The resulting dark mixture was cooled to 20-25° C. and diluted with water (50 mL). The product was extracted into 0.5M Na2CO3 (2×50 mL). The organic layer was discarded. The aqueous phases were combined and washed with CH2Cl2 (40 mL). The organic wash was discarded. The aqueous solution was acidified to pH 2.0 with 6M sulfuric acid (9.0 mL) and the product extracted into CH2Cl2 (2×20 mL). The combined CH2Cl2 layers were evaporated in vacuo. The residue was redissolved in isopropanol (75 mL) at 75° C. and the solution was treated with activated charcoal (0.85 g) at 75-80° C. for 20 min. The charcoal was removed by filtration and washed with hot isopropanol. The combined filtrate and wash was concentrated in vacuo to 40 mL. The resulting slurry was cooled slowly with stirring to 10° C. and stirred for 1 h. The solid was filtered, washed with cold isopropanol (10 mL) and dried in vacuo at 40-45° C. to afford methyl 3-hydroxy-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate as an off-white crystalline solid (3.68 g).

후처리

  1. extractionThe product was extracted into 0.5M Na2CO3 (2×50 mL)
  2. washwashed with CH2Cl2 (40 mL)
  3. washThe organic wash
  4. extractionthe product extracted into CH2Cl2 (2×20 mL)
  5. customThe combined CH2Cl2 layers were evaporated in vacuo
  6. dissolutionThe residue was redissolved in isopropanol (75 mL) at 75° C.
  7. additionthe solution was treated with activated charcoal (0.85 g) at 75-80° C. for 20 min
  8. customThe charcoal was removed by filtration
  9. washwashed with hot isopropanol
  10. washThe combined filtrate and wash
  11. concentrationwas concentrated in vacuo to 40 mL
  12. temperatureThe resulting slurry was cooled slowly
  13. stirringstirred for 1 h
  14. filtrationThe solid was filtered
  15. washwashed with cold isopropanol (10 mL)
  16. customdried in vacuo at 40-45° C.

출처 및 근거

ORD 기록
ord-2817c590dbaf49d681a04ed268b61129
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893055B2

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