6-Chloropurine → HCID 3816971, compound

HRID 380445Notes

Reaction equation

HRID 380445 reaction equation
[Na].Cl[C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[NH:5][CH:6]=[N:7]2.[CH2:12]([O:15]CC=C)[CH:13]=[CH2:14].[Na]>C(O)C=C>[CH2:12]([O:15][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[NH:5][CH:6]=[N:7]2)[CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 53592776-ChloropurineHCID 5360545SodiumHCID 86738583HCID 86738583, compound

Product 1

HCID 3816971HCID 3816971, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 7858Allyl AlcoholSolvent

Conditions

Temperature
100 °C

Procedure

Sodium (2.0 g, 86.96 mmol) was added to distilled allyl alcohol (35 ml) under nitrogen. 6-Chloropurine (1.0 g, 6.47 mmol) was dissolved in distilled allyl alcohol (35 ml) and the sodium allyloxide solution (33 ml) was added. The reaction was heated to 100° C. for 20 h, under nitrogen. After cooling, neutralisation of the reaction mixture, followed by recrystallisation of the residue from water, gave a white crystalline solid (550 mg, 48%), m.p. 199-200° C.; (Found: C, 54.35; H, 4.49; N. 32.06. Calc. for C8H8N4O: C, 54.54; H, 4.58; N, 31.80%); νmax (cm−1) 3052, 2977, 2811 (NH, C—H) δH (200 MHz, d6-DMSO) 8.526 (1H, s, C(2)H or C(8)H), 8.438 (1H, s, C(2)H or C(8)H). 6.280-6.086 (1H, dddd, CH═CH2), 5.485 (1H, dd, Jgem=1.5Hz, Jtrans=17.2 Hz, ═CH2), 5.325 (1H, dd, Jgem=1.5 Hz, Jcis=10.4 Hz, ═CH2), 5.107 (2H, d, J=5.5 Hz, OCH2); m/z 176 (M+, 43%), 174 (M+, 43%), 161 (31), 147 (39), 136 ([MH—CH2CH═CH2]+, 21%), 120 ([MH—OCH2CH═CH2]+, 49%), 108 (13), 93 (37), 81 (11), 69 (32), 66 (18), 53 (26), 41 ([CH2CH═CH2]+, 63%), 28 (62);

Workup

  1. distillationto distilled allyl alcohol (35 ml) under nitrogen
  2. temperatureAfter cooling
  3. customneutralisation of the reaction mixture, followed by recrystallisation of the residue from water

Sources & evidence

ORD record
ord-c5d99a98a5e34a43af12c52ae3488686
Source dataset
uspto-grants-2001_10
Patent number
US06303618B1

Reaction notes

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