Sodium Hydroxide → N-[4-(3-butyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-phenyl]-acetamide

HRID 720623

Reaction equation

HRID 720623 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([NH:14][C:15]2[C:16](=[O:27])[NH:17][C:18](=[O:26])[N:19]([CH2:22][CH2:23][CH2:24][CH3:25])[C:20]=2[NH2:21])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[OH-].[Na+]>CO>[CH2:22]([N:19]1[C:20]2[N:21]=[C:12]([CH2:11][C:8]3[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=3)[NH:14][C:15]=2[C:16](=[O:27])[NH:17][C:18]1=[O:26])[CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 218916952-(4-acetylamino-phenyl)-N-(6-amino-1-butyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acetamide

Product 1

HCID 21891817N-[4-(3-butyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-phenyl]-acetamideYield 62.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(4-acetylamino-phenyl)-N-(6-amino-1-butyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acetamide (330 mg, 0.88 mmol) in methanol (7.0 mL) was treated with a 10% aqueous sodium hydroxide solution (3.54 mL). The resulting solution was stirred at 25° C. for 5 min and then was heated to 50° C. for 3 h. At this time, another portion of a 10% aqueous sodium hydroxide solution (3.54 mL) was added. The reaction was heated to 50° C. for an additional 4 h. At this time, the reaction was concentrated in vacuo. The residue was cooled to 0° C. and then treated with a 1N aqueous hydrochloric acid solution. The resulting precipitate was collected by filtration, washed with water, and dried in vacuo to afford N-[4-(3-butyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-phenyl]-acetamide (196 mg, 62%) as an orange-yellow solid: 1H NMR (DMSO-d6, 300 MHz) δ 13.32 (broad s, 1H), 10.96 (broad s, 1H), 9.94 (broad s, 1H), 7.48 (d, J=8.42 Hz, 2H), 7.17 (d, J=8.42 Hz, 1H), 3.95 (s, 2H), 3.86 (m, 2H), 1.99 (s, 3H), 1.59 (m, 2H), 1.27 (m, 2H), 0.87 (t, J=7.32 Hz, 3H).

Workup

  1. temperaturewas heated to 50° C. for 3 h
  2. temperatureThe reaction was heated to 50° C. for an additional 4 h
  3. concentrationAt this time, the reaction was concentrated in vacuo
  4. temperatureThe residue was cooled to 0° C.
  5. additiontreated with a 1N aqueous hydrochloric acid solution
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-f54abc4be7444b97a241f102d0b39b63
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Linked notes

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