2,2-Dimethoxypropane → 9-(2-(2,2-Dimethyl-1,3-dioxan-5-yl)ethyl)-9H-purin-2-amine

HRID 5869

反応式

HRID 5869 の反応式
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])=[CH:4][N:3]=1.O.[C:19]1(C)[CH:24]=CC(S(O)(=O)=O)=C[CH:20]=1.COC(OC)(C)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]2[CH2:16][O:17][C:19]([CH3:24])([CH3:20])[O:15][CH2:14]2)=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 64952,2-DimethoxypropaneHCID 11430Potassium CarbonateHCID 1285176-DeoxypenciclovirHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 109567979-(2-(2,2-Dimethyl-1,3-dioxan-5-yl)ethyl)-9H-purin-2-amine収率 94.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine (240 mg, 1.0 mmol) in N,N-dimethylformamide (3 ml) were added p-toluenesulphonic acid monohydrate (210 mg, 1.1 mmol) and 2,2-dimethoxypropane (0.62 ml, 5.0 mmol) and the solution was stirred for 30 minutes. Potassium carbonate (110 mg, 0.8 mmol) was added and the solution was stirred for a further 30 minutes. Water (10 ml) was added and the solution was extracted with chloroform (3×8 ml). The organic layers were combined, dried (magnesium sulphate) and the solvent removed. Trituration with toluene-ether afforded 2-amino-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine as a white crystalline solid (262 mg, 94%) which was recrystallised from ethyl acetate-hexane (216 mg, 78%), m.p. 118°-120°; λmax (MeOH) 221 (27,200), 244 (4,920), and 308 (7,130)nm; νmax (KBr) 3450, 3140, 1635, 1615, 1580, and 1435 cm-1 ; δH [(CD3)2SO] 1.26 (3H, s, CH3), 1.33 (3H, s, CH3), 1.58 (1H, m, 3'-H), 1.74 (2H, q, J 7.1 Hz, 2'-H), 3.54 (2H, dd, J 11.8 Hz and 8.5 Hz, 2×Hax), 3.78 (2H, dd, J 11.8 Hz and 4.4 Hz, 2×Heq), 4.07 (2H, t, J 7.2 Hz, 1'-H), 6.46 (2H, s, D2O exchangeable, 2-NH2), 8.09 (1H, s, 8-H), and 8.56 (1H, s, 6-H); (Found: C, 56.09; H, 6.91; N, 24.88%. C13H19N5O2 requires C, 56.30; H, 6.91; N, 25.25%).

後処理

  1. stirringthe solution was stirred for a further 30 minutes
  2. extractionthe solution was extracted with chloroform (3×8 ml)
  3. dry with materialdried (magnesium sulphate)
  4. customthe solvent removed

出典と根拠

ORDレコード
ord-d85e608d23ee4bf4b2252ac1137409a6
出典データセット
uspto-grants-1993_09
特許番号
US05246937

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