Ethanol → 6-ethoxy-9H-purin-2-amine

HRID 380448

Reaction equation

HRID 380448 reaction equation
[Na].[CH2:2]([OH:4])[CH3:3].[NH2:5][C:6]1[N:14]=[C:13]2[C:9]([NH:10][CH:11]=[N:12]2)=[C:8](Cl)[N:7]=1>C(O)(=O)C>[CH3:3][CH2:2][O:4][C:8]1[C:9]2[NH:10][CH:11]=[N:12][C:13]=2[N:14]=[C:6]([NH2:5])[N:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 53603492-Amino-6-chloropurineHCID 5360545Sodium2×

Product 1

HCID 958056-ethoxy-9H-purin-2-amineYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium (0.5 g, 22 mmol) was added to anhydrous ethanol (50 ml) under nitrogen. When all of the sodium had reacted, 2-amino-6-chloropurine (750 mg, 4.42 mmol) was added. The reaction was refluxed for 3 h. After cooling, the reaction mixture was neutralised with glacial acetic acid and the solvent was removed. Recrystallisation from water gave the product as a white solid (548 mg, 69%), m.p.>230° C.; (Found: C, 46.76; H, 4.97; N, 39.09. Calc. for C7H9N5O: C, 46.92; H, 5.06; N, 39.09%); νmax (cm−1) 3505, 3484, 3432, 3324, 3191, 3110, 2984, 2901, 2705, 2544 (NH, C—H, NH2); δH (200 MHz, d6-DMSO) 7.808 (1H, s, C(8)H), 6.224 (2H, s, NH2), 4.437 (2H, q, J=7.1 Hz, OCH2), 1.353 (3H, t, J=7.1 Hz. CH2CH3); m/z 179 (M+, 100%), 169 (19), 164 (35), 151 ([MH—Et]+, 36%), 135 ([MH—OEt]+, 43%), 131 (38), 119 (34), 109 (54), 81 (41), 69 (39), 60 (21), 55 (31), 41 (48),

Workup

  1. temperatureThe reaction was refluxed for 3 h
  2. temperatureAfter cooling
  3. customthe solvent was removed
  4. customRecrystallisation from water

Sources & evidence

ORD record
ord-144cb77325304dc9854da007f1f1ccad
Source dataset
uspto-grants-2001_10
Patent number
US06303618B1

Linked notes

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