9-Trityladenine → HCID 3007960, compound

HRID 2417225Notes

Reaction equation

C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:16]=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[NH2:17])C=CC=CC=1.[Cl:30][CH2:31][CH2:32][O:33][CH2:34]Cl>C(Cl)Cl>[Cl:30][CH2:31][CH2:32][O:33][CH2:34][N:15]1[C:14]2[C:9](=[N:10][CH:11]=[N:12][C:13]=2[NH2:17])[N:8]=[CH:16]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 11 (1.79 g, 4.74 mmol) in CH2Cl2 (70 mL) was added (2-chloroethoxy)methyl chloride (0.65 g, 5.0 mmol). The reaction mixture was stirred at 25° C. for 8.0 h to afford a solid. Filteration and crystallization from MeOH gave 12 (1.66 g, 4.27 mmol) in 90% yield: mp 184-186° C.; Rf (hexanes/EtOAc=1:2) 0.28; UV (EtOH) λmax 267 (ε 14,600); 1H NMR (DMSO-d6) δ 3.73 (t, J=4.5 Hz, 2 H, CH2Cl), 3.86 (t, J=4.5 Hz, 2 H, OCH2), 5.76 (s, 2 H, H2C1′), 8.49 (s, 1 H, HC2), 8.74 (s, 1 H, HC8), 9.32, 10.05 (2 br, 2 H, NH2); 13C NMR (DMSO-d6) δ 43.13 (CH2Cl), 68.82 OCH2 78.10 (C1′), 118.20 (C5), 143.53 (C2), 146.50 (C8), 149.39 (C4), 151.60 (C6); MS m/z 227 (M+, Cl-cluster). Anal. (C8H10ClN5O) C, H, N, Cl; calcd (%): 42.20, 4.43, 30.76, 15.59; found (%): 42.32, 4.50, 30.69, 15.62.

Workup

customto afford a solid
customFilteration and crystallization from MeOH

Sources & evidence

ORD record: ord-de5041d571a148d3a67963683ec3cd26
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825348B2

Reaction notes

Loading…