Methanol → HCID 22160584, compound

HRID 1089290Notes

Reaction equation

HRID 1089290 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH:12]([CH2:15][CH2:16][OH:17])[CH2:13][OH:14])=[CH:4][N:3]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19].[CH3:25]O.CN(C)[CH:29]=[O:30]>CN(C)C1C=CN=CC=1>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH:12]([CH2:15][CH2:16][O:17][C:29](=[O:30])[CH3:25])[CH2:13][O:14][C:18](=[O:20])[CH3:19])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 14814219HCID 14814219, compound

Product 1

HCID 22160584HCID 22160584, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A solution of 2-amino-9-(1,4-dihydroxybut-2-oxy)purine (100 mg, 0.42 mmol), 4-dimethylaminopyridine (4 mg) and acetic anhydride (0.14 ml, 1.5 mmol) in N,N-dimethylformamide (3 ml) was stirred at room temperature for 15 minutes and methanol (0.5 ml) was then added. The solvent was removed and the residue was partitioned between chloroform (5 ml) and aqueous sodium bicarbonate (3 ml). The aqueous layer was extracted with chloroform again (5 ml) and the combined organic extracts were dried (magnesium sulphate) and the solvent removed. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol (30:1). Trituration with hexane-ethyl acetate afforded 2-amino-9-(1,4-diacetoxybut-2-oxy)purine as white crystals (112 mg, 83%), m p. 123°-125° C.; IR: υmax (KBr) 3400, 3310, 3190, 1735, 1640, 1615, 1585, 1505, 1470 and 1430 cm-1 ; 1H NMR: δH [(CD3)2SO] 2.0-2.5 (8H, m, 3'-H and 2×CH3), 4.21 (1H, dd, J=12.7 Hz and 5.8 Hz, 1'-H), 4.32 (1H, dt, Jd =10.9 Hz and Jt =5.4 Hz, 4'-H), 4.54 (1H, dd, J=12.9 Hz and 2.8 Hz, 1'-H), 4.63 (1H, m, 2'-H), 4.81 (1H, ddd, J=11.3 Hz, 9.4 Hz and 4.4 Hz, 4'-H), 5.16 (2h, s, D2O exchangeable, 2-NH2), 7.96 (1H, 8-H) and 8.67 (1H, s, 6-H). Found: C, 48.15; H, 5.23; N, 21.51%. C13H17N5O5Requires C, 48.29; H, 5.30; N, 21.66%.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between chloroform (5 ml) and aqueous sodium bicarbonate (3 ml)
  3. extractionThe aqueous layer was extracted with chloroform again (5 ml)
  4. dry with materialthe combined organic extracts were dried (magnesium sulphate)
  5. customthe solvent removed
  6. customThe residue was purified by column chromatography on silica gel eluting with chloroform-methanol (30:1)

Sources & evidence

ORD record
ord-9b2be9931ba2470faf1e58defe9ec812
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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