5-Formyluracil → HCID 178440763, compound

HRID 493113Notes

Reaction equation

HRID 493113 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:25][C:14]3=[N:15][CH:16]=[CH:17][C:18]([N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[C:13]3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:26]([C:28]1[C:29](=[O:35])[NH:30][C:31](=[O:34])[NH:32][CH:33]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:25][C:14]3=[N:15][CH:16]=[CH:17][C:18]([N:19]4[CH2:20][CH2:21][N:22]([CH2:26][C:28]5[C:29](=[O:35])[NH:30][C:31](=[O:34])[NH:32][CH:33]=5)[CH2:23][CH2:24]4)=[C:13]3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3045905-FormyluracilHCID 5049666Sodium triacetoxyborohydrideHCID 178440762HCID 178440762, compound

Product 1

HCID 178440763HCID 178440763, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-(4-tert-Butyl-phenyl)-7-piperazin-1-yl-3H-imidazo[4,5-b]pyridine (7) (50 mg, 0.15 mmol) and 5-formyluracil (21 mg, 0.15 mmol) were dissolved in NMP (4 ml) and sodium triacetoxyborohydride (64 mg, 0.30 mmol) was added. The reaction mixture was allowed to stir for 18 h under nitrogen. It was judged complete by MS, and purified by HPLC Method E to yield the title product 9 (25 mg (36%), 0.054 mmol). 1H NMR (DMSO-d6): δ 11.45 (s, 1H), 11.30 (d, J=3 Hz, 1H), 9.85(bs, 1H), 8.11 (d, J=8.3 Hz, 3H), 7.74 (d, J=6.1 Hz, 1H), 7.54 (d, J=8.3 Hz, 2H), 6.78 (s, 1H), 4.05 (s, 2H), 3.20-3.65 (m, 8H), 1.33 (s, 9H). (ESI-POS): [M+H]+=460; MS(ESI-NEG):[M−H]−=458.

Workup

  1. custompurified by HPLC Method E

Sources & evidence

ORD record
ord-c97270827be240d198797e5ab93ea84c
Source dataset
uspto-grants-2009_05
Patent number
US07534796B2

Reaction notes

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