Sodium hydride → tert-Butyl {4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetate

HRID 403469Notes

Reaction equation

HRID 403469 reaction equation
[F:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[OH:8].[H-].[Na+].[C:11]([O:15][C:16](=[O:44])[CH2:17][O:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([C:26]2[O:27][C:28]3[N:29]=[C:30](S(C)(=O)=O)[N:31]=[C:32]([O:35][CH2:36][CH2:37][CH3:38])[C:33]=3[N:34]=2)=[CH:21][C:20]=1[CH3:43])([CH3:14])([CH3:13])[CH3:12]>CN(C)C=O>[C:11]([O:15][C:16](=[O:44])[CH2:17][O:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([C:26]2[O:27][C:28]3[N:29]=[C:30]([O:8][C@@H:3]4[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]4[F:1])[N:31]=[C:32]([O:35][CH2:36][CH2:37][CH3:38])[C:33]=3[N:34]=2)=[CH:21][C:20]=1[CH3:43])([CH3:12])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12700773(1R,2R)-2-fluorocyclohexan-1-olHCID 86679896Tert-butyl [4-(5-methanesulfonyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate

Product 1

HCID 86679899tert-Butyl {4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetateYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

26 mg of trans-2-fluoro-cyclohexanol were added under argon atmosphere at 0° C. to a suspension of 10 mg of sodium hydride (60% in mineral oil) in 2 ml of N,N-dimethylformamide. After 15 min a solution of 100 mg of [4-(5-methanesulfonyl-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester in 1 ml of N,N-dimethylformamide was slowly added. After 12 h at room temperature the mixture was quenched by the addition of water and extracted twice with ethyl acetate. The combined organic layers were dried and concentrated in vacuo. 101 mg of the title compound were obtained.

Workup

  1. customAfter 12 h at room temperature the mixture was quenched by the addition of water
  2. extractionextracted twice with ethyl acetate
  3. customThe combined organic layers were dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24f43d1ec1624cc4a7a461ab0bc7b292
Source dataset
uspto-grants-2014_06
Patent number
US08748436B2

Reaction notes

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