Ethylenediamine → HCID 11209195, compound

HRID 1157511Notes

Reaction equation

HRID 1157511 reaction equation
Cl[C:2]1[N:7]([CH2:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[C:6](=[O:17])[NH:5][C:4](=[O:18])[CH:3]=1.[H-].[Na+].[CH2:21](Br)[CH3:22].C([O-])(O)=O.[Na+].[CH2:29]([NH2:32])[CH2:30][NH2:31]>C1COCC1.CS(C)=O.CO>[NH2:31][CH2:30][CH2:29][NH:32][C:2]1[N:7]([CH2:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[C:6](=[O:17])[N:5]([CH2:21][CH3:22])[C:4](=[O:18])[CH:3]=1

Participants

8

Reactant 5

HCID 3301EthylenediamineHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 113574682-((6-Chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile

Product 1

HCID 11209195HCID 11209195, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21830753dimethylsulfoxide THFSolvent

Procedure

Compound 2 (150 mg, 0.57 mmol) in THF-DMSO (6:1, 4 mL) was treated with 60% NaH (26 mg, 0.65 mmol), followed by adding ethyl bromide (300 uL). In a sealed tube, ˜20% crude product in dry MeOH (3 mL) was treated NaHCO3 and ethane-1,2-diamine (200 μL) at 120° C. for 2 h, and purified by LC-MS to give the title compound 16. 1H-NMR (400 MHz, CDCl3-CD3OD 10:1) δ 7.70 (d, J=7.8 Hz, 1H), 7.58 (t, J=7.7 Hz, 1H), 7.40 (t, J=7.4 Hz, 1H), 7.12 (d, J=8.1 Hz, 1H), 5.37 (s, 2H), 3.95 (q, J=6.8 Hz, 2H), 3.45 (t, J=5.9 Hz, 2H), 3.11 (t, J=6.1 Hz, 2H), 1.19 (t, J=6.8 Hz, 3H). MS (ES) [m+H] calc'd for C6H20N5O2, 314.2; found 314.2.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-4e7c39aa83654f25beb3186635447ceb
Source dataset
uspto-grants-2010_10
Patent number
US07807689B2

Reaction notes

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