Trityl chloride → 2-Amino-9-(triphenylmethyl)-3,9-dihydro-6H-purin-6-one

HRID 2417221Notes

Reaction equation

[NH:1]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]=[C:2]1[NH2:3].[C:12]1([C:18](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C[Si](N[Si](C)(C)C)(C)C>[C:12]1([C:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:6]2[CH:7]=[N:8][C:9]3[C:10](=[O:11])[NH:1][C:2]([NH2:3])=[N:4][C:5]2=3)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Guanine 5 (1.51 g, 9.99 mmol) and (NH4)2SO4 (100 mg) were suspended in HMDS (150 mL) and refluxed for 24 h. The solvent was evaporated under reduced pressure and the residue was dissolved in CH3CN (150 mL). Triphenylmethyl chloride (2.79 g, 10.0 mmol) was added and the reaction mixture was stirred at 25° C. for 7.0 h. The solution was concentrated under reduced pressure and the residue was purified by use of column chromatography (hexanes/EtOAc=1.5:8.5) to afford 6 (3.54 g, 8.99 mmol) in 90% yield: mp 268-270° C.; Rf(hexanes/EtOAc=1:2) 0.34; UV (EtOH) λmax 254 (ε 13,870), 278 (sh); 1H NMR (DMSO-d6) δ 5.97 (s, 2 H, NH2), 7.09-7.39 (m, 16 H, HC8+C(C6H5)3), 10.45 (br s, 1H, NH); MS m/z 393 (M+). Anal. (C24H19N5O) C, H, N; calcd (%): 73.26, 4.87, 17.80; found (%): 73.20, 4.81, 17.78.

Workup

temperaturerefluxed for 24 h
customThe solvent was evaporated under reduced pressure
dissolutionthe residue was dissolved in CH3CN (150 mL)
concentrationThe solution was concentrated under reduced pressure
customthe residue was purified by use of column chromatography (hexanes/EtOAc=1.5:8.5)

Sources & evidence

ORD record: ord-e7f77a856bdb4882b0fef0e959d7e80b
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825348B2

Reaction notes

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