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Acetic Acid → 2-Amino-9-(2,2-dimethyl-1,3-dioxan-5-ylmethoxy)-6-methoxypurine

HRID 1089269
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HRID 1089269 반응식
Cl[C:2]1[N:10]=[C:9]([NH:11]C=O)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[O:14][CH2:15][CH:16]1[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]1.[C:24](O)(=[O:26])C>C[O-].[Na+].CO>[NH2:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[O:14][CH2:15][CH:16]2[CH2:17][O:18][C:19]([CH3:22])([CH3:23])[O:20][CH2:21]2)=[C:2]([O:26][CH3:24])[N:10]=1
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참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 221605896-Chloro-9-(2,2-dimethyl-1,3-dioxan-5-ylmethoxy)-2-formamidopurine

생성물 1

HCID 198136312-Amino-9-(2,2-dimethyl-1,3-dioxan-5-ylmethoxy)-6-methoxypurine수율 69%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 10942334Sodium Methoxide용매

실험 절차

6-Chloro-9-(2,2-dimethyl-1,3-dioxan-5-ylmethoxy)-2-formamidopurine (0.5 g, 1.46 mmol) in 1.2M sodium methoxide in methanol (3.38 ml) and methanol (5 ml) was heated at reflux temperature for 1.5 hours and then cooled. Acetic acid (0.16 ml) was added and the solution evaporated to dryness. The residue was suspended in water and extracted with ethyl acetate (2×50 ml). The combined ethyl acetate extracts were washed with water, dried (magnesium sulphate) and evaporated under reduced pressure. Chromatography on silica gel (eluted with chloroform-ethanol, 100:1) gave the title compound (310 mg, 69%). 1R: υmax (KBr) 3397, 3208, 1640, 1616, 1581, 1480, 1390 cm-1. 1H NMR: δH [(CD3)2SO] 1.32(3H,s,CH3), 1.35(3H,s,CH3), 2.00(1H,m,CH), 3.77(2H,dd, J=11.8, 6.1 Hz, 2×H(ax), 3.9 (3H,s,OCH3), 3.99 (2H,dd,J=11.8, 4.1 Hz, 2×H(eq)), 4.36(2H,d, J=6.8 Hz, CH2ON), 6.60(2H,br.s, D2O exchangeable, NH2), 8.14(1H,s,H-8). Found: C, 49.30; H, 6.12; N, 22.03%; M+ 309.1455. C13H19N5O4 0.5H2O requires: C, 49.04; H, 6.34; N, 22.00%; M+ 309.1437.

후처리

  1. temperatureat reflux temperature for 1.5 hours
  2. temperaturecooled
  3. customthe solution evaporated to dryness
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. washThe combined ethyl acetate extracts were washed with water
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-39dcd7cbc1584e38af7475f4231bde4a
출처 데이터셋
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04965270

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