2-Phenylethanol → HCID 18365127, compound

HRID 380447Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].C1COCC1.Cl[C:17]1[N:25]=[CH:24][N:23]=[C:22]2[C:18]=1[NH:19][CH:20]=[N:21]2>C(O)(=O)C>[C:1]1([CH2:7][CH2:8][O:9][C:17]2[N:25]=[CH:24][N:23]=[C:22]3[C:18]=2[NH:19][CH:20]=[N:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-Phenylethanol (13 ml) was stirred under nitrogen and sodium (0.75 g, 32.36 mmol) was added. The reaction was heated to 60° C. When no sodium remained, anhydrous THF (18 ml) and 6-chloropurine (1.0 g, 6.47 mmol) were added. After refluxing under nitrogen for 5 h, the reaction mixture was allowed cool to room temperature and neutralised with glacial acetic acid. The THF was removed and the remaining alcohol was removed in vacuo. The product was recrystallised from ethanol and isolated as a white crystalline solid (962 mg, 62%), m.p. 209-210° C.; (Found: C, 64.57; H, 5.12; N, 23.54. Calc. for C13H12N4O: C, 64.99; H, 5.03; N, 23.34%); νmax (cm−1) 3135,3063, 3031, 2948, 2897, 2797, 2672, 2583 (NH, C—H); δH (200 MHz, d6-DMSO) 8.483 (1H, s, C(2)H or C(8)H), 8.365 (1H, s, C(2)H or C(8)H), 7.366-7.194 (5H, m, Ph), 4.741 (2H, t, J=7.0 Hz, OCH2), 3.134 (2H, t, J=7.0 Hz, CH2Ph); m/z 240 (M+, 11%), 149 ([M—Bn]+, 11%), 136 ([M—CH2CH2Ph]+, 87%), 119 ([M—OCH2CH2Ph]+, 40%), 104 ([CH2CH2Ph]+, 100%), 91 (BN+, 37%), 77 (Ph+, 55%), 69 (48), 65 (15), 51 (26).

Workup

temperatureAfter refluxing under nitrogen for 5 h
customThe THF was removed
customthe remaining alcohol was removed in vacuo
customThe product was recrystallised from ethanol

Sources & evidence

ORD record: ord-4686a1b51977487880eb27229155d244
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303618B1

Reaction notes

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