Water → 2,4-Dimethoxypyrimidine-5-carbaldehyde

HRID 1707954

반응식

HRID 1707954 반응식
CCCCCC.Br[C:8]1[C:9]([O:16][CH3:17])=[N:10][C:11]([O:14][CH3:15])=[N:12][CH:13]=1.[CH:18](OCC)=[O:19].O>CCOCC>[CH:18]([C:8]1[C:9]([O:16][CH3:17])=[N:10][C:11]([O:14][CH3:15])=[N:12][CH:13]=1)=[O:19]

참가 물질

6

반응물 4

HCID 962WaterHCID 8025Ethyl formateHCID 8058HexaneHCID 2557195-Bromo-2,4-dimethoxypyrimidine

생성물 1

HCID 5977822,4-Dimethoxypyrimidine-5-carbaldehyde

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-70 °C

실험 절차

A solution of 1.6M n-Buli in hexane (48 ml, 73.6 mmol) was added over 5 min. to a stirred suspension of 5-bromo-2,4-dimethoxypyrimidine (16 g; 72.9 mmol) in dry Et2O (240 ml) at -70° C. under an atmosphere of dry N2. Dry ethyl formate (28 g: 377 mmol) was added and the orange solution stirred at -70° C. for 1 h then allowed to warm slowly to ambient temperature. Water (400 ml) was added and the aqueous layer separated and extracted with Et2O (3×200 ml). The ether layer was combined with the extracts and dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography by preloading in SiO2 and eluting with EtOAc-hexane (3:7, v/v). Product fractions were combined and evaporated to give fine white needles, yield 6.89 g, (56%). Mass spectrum m/z 169 (M+H)+Analysis, found: C, 50:1;H,4.5;N,16.9%;C7H8N2O3 requires C,50.00; H,4.79; N, 16.66%.

후처리

  1. temperatureto warm slowly to ambient temperature
  2. customthe aqueous layer separated
  3. extractionextracted with Et2O (3×200 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting with EtOAc-hexane (3:7, v/v)
  9. customevaporated
  10. customto give fine white needles, yield 6.89 g, (56%)

출처 및 근거

ORD 기록
ord-d44ba53f2f18452188175c5c1e01b82f
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05356882

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