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

HRID 1089269
ノート
印刷プレビュー

反応式

HRID 1089269 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 10942334Sodium Methoxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-39dcd7cbc1584e38af7475f4231bde4a
出典データセット
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04965270

反応ノート

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