Ethanol → HCID 11012503, compound

HRID 2417226Notes

Reaction equation

HRID 2417226 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.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][O:41][CH2:42]Cl)=[CH:34][CH:33]=1.ClCCOCN1C2C(=NC=NC=2N)N=C1.CCO>C(Cl)Cl>[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][O:41][CH2:42][N:15]2[C:14]3[C:9](=[N:10][CH:11]=[N:12][C:13]=3[NH2:17])[N:8]=[CH:16]2)=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1556219-TrityladenineHCID 3007960HCID 3007960, compoundHCID 22633890HCID 22633890, compound

Product 1

HCID 11012503HCID 11012503, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After 10 h, compound 13 (2.79 g, 8.86 mmol) was synthesized in 86% yield from 11 (3.90 g, 10.3 mmol) and (2-(p-methoxyphenyloxy)ethoxy)methyl chloride (2.25 g, 10.4 mmol) in CH2Cl2 (100 mL) by the method used for the synthesis of 12: mp 129-130° C.; Rf(hexanes/EtOAc=1:2) 0.21; UV (EtOH) λmax 270 (ε 15,100); 1H NMR (CD3OD) δ 3.68 (s, 3 H, OCH3), 4.04 (br s, 4 H, O(CH2)2O), 5.83 (s, 2 H, H2C1′), 6.58, 6.68 (AA′BB′, J=9.0 Hz, 4 H, C6H4), 8.29 (s, 1 H, HC2), 8.61 (s,1 H, HC8); 13C NMR (CD3OD) δ 56.03 (CH3), 68.70 (OCH2), 70.18 CH2OPh 82.27 (C1′), 119.59 (C5), 144.17 (C2), 147.57 (C8), 150.25 (C4), 151.97 (C6), 115.50, 116.35, 153.44, 155.53 (C6H4); MS m/z 315 (M+). Anal. (C15H17N5O3) C, H, N; calcd (%): 57.13, 5.43, 22.21; found (%): 57.24, 5.49, 22.34.

Sources & evidence

ORD record
ord-9b126a651e5a420fa4dcd878f15f1864
Source dataset
uspto-grants-2004_11
Patent number
US06825348B2

Reaction notes

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