3-Nitrophenol → HCID 86679635, compound

HRID 577691Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([I:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[N:7]=1.[N+:21]([C:24]1[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([O:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=2)[C:5]2[C:10]([I:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a reaction vial was added 2,4-dichloro-5-iodo-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (3.50 g, 7.9 mmol), as prepared in Example 5, step 1, 3-nitrophenol (1.1 g, 7.9 mmol), DMF (26 mL) and K2CO3 (2.18 g, 16 mmol, 2 mol eq). The reaction mixture was stirred and heated to 60° C. (block temperature) for 1 hr. The volatiles were removed and water (30 mL) was added. Ethyl acetate (120 mL) was added and the organic layer was separated, washed with water (20 mL), brine (20 mL), dried over Na2SO4 and evaporated to give crude product (TLC: Rf 0.6 (major) and 0.4 (minor) in 20% ethyl acetate-80% heptane). The product was purified on silica to give a light yellow oil, which solidified to a light yellow solid (3.65 g, 85% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.28-8.31 (m, 1H) 8.26 (d, J=8.06 Hz, 1H) 8.02 (s, 1H) 7.90-7.94 (m, 1H) 7.83-7.89 (m, 1H) 5.60 (s, 2H) 3.53-3.67 (m, 2H) 0.84-0.99 (m, 2H) 0.00 (s, 9H). m/z (APCI+) for C18H20ClIN4O4Si 547.0 (M+H)+.

Workup

customThe volatiles were removed
additionwater (30 mL) was added
additionEthyl acetate (120 mL) was added
customthe organic layer was separated
washwashed with water (20 mL), brine (20 mL)
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-5dd42cab8ba2470faa3017565b0ac6aa
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040547B2

Reaction notes

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