Ethanol → HCID 135407768, compound

HRID 2417223Notes

Reaction equation

HRID 2417223 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:16]=[N:15][C:14]3[C:13](=[O:17])[NH:12][C:11]([NH2:18])=[N:10][C:9]2=3)C=CC=CC=1.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][O:42][CH2:43]Cl)=[CH:35][CH:34]=1.CCO>CN(C=O)C>[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][O:42][CH2:43][N:15]2[C:14]3[C:13](=[O:17])[NH:12][C:11]([NH2:18])=[N:10][C:9]=3[N:8]=[CH:16]2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 22633890HCID 22633890, compoundHCID 1361340242-Amino-9-(triphenylmethyl)-3,9-dihydro-6H-purin-6-one

Product 1

HCID 135407768HCID 135407768, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 8 (2.72 g, 8.20 mmol) was prepared in 82% yield from 6 (3.64 g, 9.25 mmol) and (2-(p-methoxyphenyloxy)ethoxy)methyl chloride (2.18 g, 10.1 mmol) in DMF (100 mL) by the method used for the synthesis of 7: mp>250° C. (dec.); Rf(hexanes/EtOAc=1:2) 0.18; UV (EtOH) λmax 290 (ε 16,500); 1H NMR (DMSO-d6) δ 3.70 (s, 3 H, OCH3), 4.02-4.10 (m, 4 H, O(CH2)2O), 5.74 (s, 2 H, H2C1′), 5.88 (s, 2 H, NH2), 6.67, 6.70 (AA′BB′, J=9.30 Hz, 4 H, C6H4), 7.50 (s, 1 H, NH), 8.85 (s, 1 H, HC8); 13C NMR (DMSO-d6) δ 56.12 (CH3), 68.74 (OCH2), 70.20 (CH2Oph), 75.31(C1′), 107.25 (C5), 144.02 (C8), 153.25 (C4), 154.48 (C2), 159.26 (C6), 115.55, 116.38, 153.51, 155.56 (C6H4); MS m/z 331 (M+). Anal (C15H17N5O4) C, H, N; calcd (%): 54.37, 5.17, 21.13; found (%): 54.26, 5.20, 21.19.

Workup

  1. customused for the synthesis of 7

Sources & evidence

ORD record
ord-38f3ba1afcd04c1a87118d668da16c9b
Source dataset
uspto-grants-2004_11
Patent number
US06825348B2

Reaction notes

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