Sodium Carbonate → O6-benzyl-2-fluorohypoxanthine

HRID 1416913노트

반응식

HRID 1416913 반응식
[CH:1]1[CH:2]=[CH:3][C:4]([CH2:7][O:8][C:9]2[C:10]3[N:14]=[CH:13][NH:12][C:11]=3[N:15]=[C:16](N)[N:17]=2)=[CH:5][CH:6]=1.[H+].[B-](F)(F)(F)[F:21].N([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O>[CH:1]1[CH:2]=[CH:3][C:4]([CH2:7][O:8][C:9]2[C:10]3[NH:14][CH:13]=[N:12][C:11]=3[N:15]=[C:16]([F:21])[N:17]=2)=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 28118Tetrafluoroboric acid4회HCID 23668193Sodium Nitrite3회HCID 178508945HCID 178508945, 화합물

생성물 1

HCID 563585O6-benzyl-2-fluorohypoxanthine

시약·촉매·용매 1

HCID 962Water용매

실험 절차

O6 -Benzylguanine (1.21 g, 5 mmol) was added to 100 mL of 48% fluoboric acid at -20° C. Sodium nitrite (1.23 g, 35 mmole) was dissolved in water (5 mL) and 2.5 mL of this sodium nitrite solution was added slowly to the cold fluoboric acid solution. The resulting mixture was stirred for 1 h at or below -15° C. Additional fluoboric acid (25 mL) was added followed by an additional 2.5 mL of the aqueous sodium nitrite solution. After stirring for an additional 1 h below -15° C., fluoboric acid (25 mL) was again added and stirring was continued for 1 h. The resulting solution was neutralized with saturated aqueous sodium carbonate solution at -20° C. and was allowed to warm to room temperature. A white precipitate that formed was collected by filtration and was washed with water and dried under vacuum to afford crude 4c: yield, 0.52 g, 43%. An analytical sample was prepared by chromatography on a Sephadex LH-20 column (3×80 cm) eluted with methanol/water (1:1) at 1 mL/min. The desired 4c eluted in fractions 66-77: mp 182-183° C. (184-185° C.; Robins and Robins, J. Org. Chem., 34, 2160-2163 (1969)); UV (pH 1) λmax 256 nm (ε=1.117×104); (pH 6.9) 257 (1.078×104); (pH 13) 264 (1.063×104); 1H NMR δ 5.60 (s, 2H, ArCH2), 7.37-7.57 (m, 5H, ArH), 8.40 (s, 1H, H-8), 13.60 (s, 1H, NH, exchanges with D2O),19F NMR δ 23.54 downfield from trifluoroacetic acid standard; MS (EI) calcd. m/z for C12H9FN4O 244.0760, found 244.0756; Anal. (C12H9FN4O.2/3 H2O) C, H, N.

후처리

  1. stirringAfter stirring for an additional 1 h below -15° C.
  2. stirringstirring
  3. waitwas continued for 1 h
  4. customA white precipitate that formed
  5. filtrationwas collected by filtration
  6. washwas washed with water
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-f9f73bb46fe442548ac2c0603fe04d09
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05916894

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