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

HRID 81507Notes

Reaction equation

HRID 81507 reaction equation
[F:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[OH:8].[H-].[Na+].CS([C:15]1[N:16]=[C:17]([O:41][CH2:42][CH2:43][CH3:44])[C:18]2[N:23]=[C:22]([C:24]3[CH:38]=[C:37]([CH3:39])[C:27]([O:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[C:26]([CH3:40])[CH:25]=3)[O:21][C:19]=2[N:20]=1)(=O)=O>CN(C)C=O>[F:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[O:8][C:15]1[N:16]=[C:17]([O:41][CH2:42][CH2:43][CH3:44])[C:18]2[N:23]=[C:22]([C:24]3[CH:25]=[C:26]([CH3:40])[C:27]([O:28][CH2:29][C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])=[C:37]([CH3:39])[CH:38]=3)[O:21][C:19]=2[N:20]=1

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}acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under an atmosphere of argon and at 0 C, 26 mg of trans-2-fluorocyclohexanol were added 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 tert-butyl [4-(5-methanesulfonyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate in 1 ml of N,N-dimethylformamide was slowly added. After 12 h at room temperature, the mixture was quenched by addition of water and extracted twice with ethyl acetate. The combined organic layers were dried and concentrated under reduced pressure. This gave 101 mg of the title compound.

Workup

  1. waitAfter 12 h at room temperature
  2. customthe mixture was quenched by addition of water
  3. extractionextracted twice with ethyl acetate
  4. customThe combined organic layers were dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b471f888480945b7ae876a55e18b2f8f
Source dataset
uspto-grants-2014_09
Patent number
US08846691B2

Reaction notes

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