Nitrogen → HCID 68379366, compound

HRID 330733Notes

Reaction equation

HRID 330733 reaction equation
N#N.[CH2:3]([O:10][C@H:11]1[C@H:15]([OH:16])[C@@H:14]([CH2:17][OH:18])[O:13][C@H:12]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][CH:22]=[N:23][C:24]=2[O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:35][O:36][C:37]1[CH:58]=[CH:57][C:40]([C:41](Cl)([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:42]2[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=2)=[CH:39][CH:38]=1>N1C=CC=CC=1.ClCCl.CCOC(C)=O.CCCCCC.C(N(CC)CC)C>[CH3:49][O:48][C:45]1[CH:44]=[CH:43][C:42]([C:41]([C:40]2[CH:39]=[CH:38][C:37]([O:36][CH3:35])=[CH:58][CH:57]=2)([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[O:18][CH2:17][C@H:14]2[O:13][C@@H:12]([N:19]3[CH:27]=[N:26][C:25]4[C:20]3=[N:21][CH:22]=[N:23][C:24]=4[O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C@@H:11]([O:10][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[C@@H:15]2[OH:16])=[CH:47][CH:46]=1

Participants

9

Reactant 3

HCID 947NitrogenHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 68379651HCID 68379651, compound

Product 1

HCID 68379366HCID 68379366, compoundYield 44.4%

Reagents, catalysts & solvents 5

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Under the protection of N2, to a solution of 9-(2-O-benzyl-β-D-arabinofuranosyl)-6-[2-(trimethylsilyl)ethoxy]-9H-purine (1.60 g, 3.49 mmol) in 20 mL pyridine was added 4,4′-dimethoxytrityl chloride (2.13 g, 6.28 mmol). The mixture was stirred at room temperature for 2 h. The reaction was diluted with 100 mL dichloromethane and quenched with 100 mL saturated NaHCO3 solution. After the aqueous layer was extracted with dichloromethane (100 mL) three times, the organic layers were combined and evaporated. The residue was purified by flash chromatography (gradient: hexane with EtOAc 0-100%, with 1% triethylamine in both hexane and EtOAc) to produce 1.18 g (1.55 mmol, 44.4%) product. LCMS: for C43H48N4O7Si calculated 760.9. found 762.5 [M+H]+. 1H NMR (600 MHz, CD3CN) δ: 8.39 (s, 1H), 8.10 (s, 1H), 7.42-7.40 (m, 2H), 7.29-7.13 (m, 10H), 6.86-6.85 (m, 2H), 6.81-6.77 (m, 4H), 6.50 (d, J=5.5 Hz, 1H), 4.69-4.65 (m, 2H), 4.49-4.45 (m, 2H), 4.24-4.21 (m, 2H), 4.02 (m, 1H), 3.8 (dd, 10.4, 6.3 Hz, 1H), 3.29 (dd, J=10.4, 3.5 Hz, 1H), 1.22 (m, 2H), 0.09 (s, 1H). 13C NMR (600 MHz, CD3CN) δ: 160.82, 152.01, 142.44, 130.24, 130.21, 128.39, 128.25, 128.01, 127.86, 127.61, 127.05, 113.21, 83.56, 82.87, 82.37, 74.31, 72.54, 65.26, 63.56, 55.10, 17.27, −2.13.

Workup

  1. customquenched with 100 mL saturated NaHCO3 solution
  2. extractionAfter the aqueous layer was extracted with dichloromethane (100 mL) three times
  3. customevaporated
  4. customThe residue was purified by flash chromatography (gradient

Sources & evidence

ORD record
ord-c8a0439acf424376a93f954532d0131b
Source dataset
uspto-grants-2014_11
Patent number
US08877439B2

Reaction notes

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