Sodium hydride → HCID 86619891, compound

HRID 2388865Notes

Reaction equation

HRID 2388865 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=1.FC1C(F)=CC=CC=1CSC1N=C(NS(N2CCC2)(=O)=O)C=C([O:43][CH:44]([CH2:47]O)[CH2:45]O)N=1.[H-].[Na+]>CC(O)C>[Cl:8][C:6]1[CH:7]=[C:2]([O:43][CH:44]([CH3:47])[CH3:45])[N:3]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11698344N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[2-hydroxy-1-(hydroxymethyl)ethoxy]-4-pyrimidinyl]-1-azetidinesulfonamideHCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

Product 1

HCID 86619891HCID 86619891, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4,6-dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine ((the product of example 1 step 3 g) in propan-2-ol (20 ml) was added NaH (0.43 g) slowly and the reaction was then allowed to stir overnight at RT. The reaction mixture was then partitioned between DCM (100 ml) and H2O (100 ml). The organics were separated and the aqueous layer was re-extracted with DCM (2×100 ml). Organics were combined, dried (MgSO4) and reduced in vacuo to give the subtitle compound as a pale yellow solid. Yield: 1.8 g

Workup

  1. customThe reaction mixture was then partitioned between DCM (100 ml) and H2O (100 ml)
  2. customThe organics were separated
  3. extractionthe aqueous layer was re-extracted with DCM (2×100 ml)
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-5776ef8ffb864b16a9ff99160627adc7
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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