Hydrochloric Acid → 1-trityl-1H-imidazole-4-carboxylic acid {4-[3-butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amide

HRID 720641Notes

Reaction equation

HRID 720641 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]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([C:35]2[N:36]=[CH:37][N:38]([C:40]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:39]=2)=[O:34])=[CH:28][CH:27]=1)=O.[OH-].[Na+].Cl>CO>[CH2:8]([N:7]1[C:2]2[N:1]=[C:23]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([NH:32][C:33]([C:35]4[N:36]=[CH:37][N:38]([C:40]([C:47]5[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=5)([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)[C:53]5[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=5)[CH:39]=4)=[O:34])=[CH:30][CH:31]=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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 587392571-trityl-1H-imidazole-4-carboxylic acid (4-{[6-amino-1-butyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-amide

Product 1

HCID 587392591-trityl-1H-imidazole-4-carboxylic acid {4-[3-butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amideYield 69.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 1-trityl-1H-imidazole-4-carboxylic acid (4-{[6-amino-1-butyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-amide (68.5 mg, 0.09 mmol) in methanol (2.0 mL) at 25° C. was treated with a 10% aqueous sodium hydroxide solution (1.06 mL, 0.26 mmol). The reaction was then warmed to 50° C. for 1 h. At this time, additional methanol (1.0 mL) was added. The reaction was continued at 50° C. for 2.5 h. At this time, the reaction was treated with a 3N aqueous hydrochloric acid solution (0.88 mL) and was stirred for 10 min. The resulting solid was collected by filtration, washed with water, and was dried in vacuo to afford 1-trityl-1H-imidazole-4-carboxylic acid {4-[3-butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amide (46.6 mg, 69.6%): EI-HRMS m/e calcd for C46H40N7O3F (M+) 757.3177, found 757.3160.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water
  3. customwas dried in vacuo

Sources & evidence

ORD record
ord-ba309d8080b34347abdb1e71560bed7e
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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