Sodium Hydroxide → HCID 10370621, compound

HRID 858076Notes

Reaction equation

HRID 858076 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH2:10][CH3:11])[C:6](=[O:12])[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[C:4](=[O:21])[C:3]=1[NH:22][C:23](=O)[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](=[O:40])(=[O:39])[NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[CH:27][CH:26]=1.[OH-].[Na+]>CO>[CH2:8]([N:7]1[C:2]2[N:1]=[C:23]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([S:31]([NH:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)(=[O:39])=[O:40])=[CH:29][CH:30]=3)[NH:22][C:3]=2[C:4](=[O:21])[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[C:6]1=[O:12])[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 45118824N-{6-Amino-1-butyl-3-[(2-fluorophenyl)methyl]-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl}-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}acetamide

Product 1

HCID 10370621HCID 10370621, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of crude N-[6-amino-1-butyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-2-[4-(pyridin-2-ylsulfamoyl)-phenyl]-acetamide (50 mg, 0.86 mmol) in methanol (5 mL) was treated with a 10% w/v aqueous sodium hydroxide solution (0.1 mL, 0.25 mmol). The resulting solution was heated to reflux for until all of the starting material had been consumed. At this time, the reaction mixture was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 5/95 methanol/methylene chloride) followed by trituration with cold methanol afforded 4-[3-butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-N-pyridin-2-yl-benzenesulfonamide (14.7 mg, 26% from [4-(pyridin-2-ylsulfamoyl)-phenyl]-acetic acid) as a colorless solid; 1H NMR(DMSO-d6, 300 MHz) δH 13.50 (broad s, 1H), 7.90 (broad s, 1H), 7.74 (d, J=8.1 Hz, 2H), 7.63 (t, J=7.3 Hz, 1H), 7.37 (d, J=7.7 Hz, 2H), 7.30–6.95 (m, 5H), 6.77 (broad s, 1H), 5.02 (s, 2H), 4.06 (s, 2H), 3.87 (t, J=7.1 Hz, 2H), 1.54 (t, J=7.0 Hz, 2H), 1.17 (q, J=7.5 Hz, 2H), 0.77 (t, J=7.3 Hz, 3H); FAB-HRMS m/e calculated for C28H27FN6O4S (M+H)+ 563.1877, found 563.1860.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for until all of the starting material
  3. customhad been consumed
  4. concentrationAt this time, the reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-df9b02bc56eb47508ef0915cb6771eff
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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