Sodium Hydroxide → HCID 178503039, compound

HRID 1525251Notes

Reaction equation

HRID 1525251 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:21][C:22]([C:24]2[C:25]([OH:35])=[N:26][C:27]([N:30]3[CH:34]=[CH:33][CH:32]=[N:31]3)=[N:28][CH:29]=2)=[O:23])[C:9]2[CH:14]=[CH:13][C:12]([P:15]([CH3:20])(=[O:19])[O:16]CC)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([NH:21][C:22]([C:24]2[C:25]([OH:35])=[N:26][C:27]([N:30]3[CH:34]=[CH:33][CH:32]=[N:31]3)=[N:28][CH:29]=2)=[O:23])[C:9]2[CH:10]=[CH:11][C:12]([P:15]([CH3:20])(=[O:16])[OH:19])=[CH:13][CH:14]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178476770HCID 178476770, compound2×

Product 1

HCID 178503039HCID 178503039, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 4-((4-fluorophenyl)(4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamido)methyl)phenyl(methyl)phosphinate, 17-f, (2 g, 4.03 mmol) was dissolved in 20 ml of dioxane and treated with 10 ml of 3N NaOH. The mixture was heated at 80° C. for one hour. Then the mixture was concentrated under vacuum and the residue was diluted with water and washed with ethyl acetate. The aqueous layer was acidified with conc. HCl to pH=1 and the expected product crashed out (1.7 g of crude). The product can be further purified via prep-HPLC give the title product, 17-1, (1.4 g, 75%). 1H NMR (300 MHz, CD3OD): δ 8.66 (s, 1H), 8.59 (s, 1H), 7.93 (s, 1H), 7.81 (m, 2H), 7.50 (m, 2H), 7.36 (m, 2H), 7.10 (m, 2H), 6.66 (s, 1H), 6.38 (s, 1H), 1.66 (d, 3H). (M+H)+=468.0.

Workup

  1. concentrationThen the mixture was concentrated under vacuum
  2. additionthe residue was diluted with water
  3. washwashed with ethyl acetate
  4. customThe product can be further purified

Sources & evidence

ORD record
ord-d870cedea3894895b6d7f0252c38a8c2
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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