Sodium Hydroxide → HCID 86752729, compound

HRID 963442Notes

Reaction equation

HRID 963442 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]([O:34][CH3:35])[C:13]([O:32][CH3:33])=[C:14]([C:16]#[C:17][C:18]3[CH:23]=[CH:22][C:21]([P:24](=[O:31])([O:28]CC)[O:25][CH2:26][CH3:27])=[CH:20][CH:19]=3)[CH:15]=2)=[CH:4][N:3]=1.[OH-].[Na+:37]>C(O)C>[Na+:37].[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]([O:34][CH3:35])[C:13]([O:32][CH3:33])=[C:14]([C:16]#[C:17][C:18]3[CH:19]=[CH:20][C:21]([P:24](=[O:28])([O-:31])[O:25][CH2:26][CH3:27])=[CH:22][CH:23]=3)[CH:15]=2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54295204HCID 54295204, compound

Product 1

HCID 86752729HCID 86752729, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

150 mg of diethyl [4-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-phenyl]-phosphonate (Example 12bo)) are dissolved in 7 ml of ethanol and treated with 2 ml of a 2N sodium hydroxide solution. The solution is held under reflux for 45 min., then cooled and chromatographed on MCl-gel with water/acetonitrile. 74 mg of monoethyl [4-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-phenyl]-phosphonate sodium salt are isolated. Yield: 50%. Mass spectrum: peaks inter alia at m/e: 491 (M++Na, 10%), 469.2 (M++H, 100%), 419.4 (15%), 413.3 (20%), 391.3 (45%).

Workup

  1. temperatureunder reflux for 45 min.
  2. temperaturecooled
  3. customchromatographed on MCl-gel with water/acetonitrile

Sources & evidence

ORD record
ord-e584f41d1a3f419cb41f0f500be9653d
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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