4-Toluenesulfonyl chloride → HCID 25187393, compound

HRID 750506Notes

Reaction equation

HRID 750506 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[C:5]([N+:9]([O-:11])=[O:10])[C:6](=[O:8])[N:7]=1.C(N(CC)CC)C.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>ClCCl>[NH2:1][C:2]1[N:7]=[C:6]([O:8][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=2)(=[O:32])=[O:31])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)[N:3]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178508996HCID 178508996, compound

Product 1

HCID 25187393HCID 25187393, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 2-amino-6-(2-furyl)-5-nitropyrimidine-4(1H)-one (1.00 g, 4.50 mmol) in dichloromethane (50 mL) was treated with triethylamine (0.941 mL, 6.75 mmol) and p-toluenesulfonyl chloride (944 mg, 4.95 mmol), stirred for 1 h, diluted with dichloromethane (50 mL), washed with 2-M HCl (20 mL), dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; isohexane:EtOAc (2:1)] to give the title compound (410 mg, 24%) as a yellow solid; NMR δH (400 MHz, CDCl3) 7.95 (2H, d, J 8.5 Hz), 7.59-7.57 (1H, m), 7.39 (2H, d, J 8.5 Hz), 7.23-7.21 (1H, m), 6.59-6.51 (1H, m), 5.39 (2H, br s), 2.48 (3H, s); Retention time 5.68 min.

Workup

  1. washwashed with 2-M HCl (20 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by chromatography [SiO2; isohexane:EtOAc (2:1)]

Sources & evidence

ORD record
ord-7f8e584c02794035ae08454143e35b9d
Source dataset
uspto-grants-2008_07
Patent number
US07405219B2

Reaction notes

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