Sodium hydride → (trans)-2-(6-Chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl)cyclopentanol

HRID 2388911Notes

Reaction equation

HRID 2388911 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(OC(CO)CO)N=1.[C@@H:49]1(O)[CH2:53][CH2:52][CH2:51][C@H:50]1[OH:54].[H-].[Na+]>C1COCC1>[Cl:8][C:6]1[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]=[C:2]([C@@H:49]2[CH2:53][CH2:52][CH2:51][C@H:50]2[OH:54])[CH:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 225711trans-1,2-CyclopentanediolHCID 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 86619895(trans)-2-(6-Chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl)cyclopentanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,6-dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of example 1 step 2.3 g) and (trans)-cyclopentane-1,2-diol (1 g) in THF (50 ml) was added NaH (0.30 g) slowly and the reaction was then allowed to stir for 18 h at RT. The reaction mixture was then partitioned between DCM (150 ml) and H2O (100 ml). The organics were separated and the aqueous layer was re-extracted with DCM (2×150 ml). Organics were combined, dried (MgSO4) and reduced in vacuo and the resulting clear oil was purified by column chromatography on silica gel EtOAc/iso-Hexane (2:8) to give the subtitle compound as a clear colourless oil. Yield 0.94 g

Workup

  1. customThe reaction mixture was then partitioned between DCM (150 ml) and H2O (100 ml)
  2. customThe organics were separated
  3. extractionthe aqueous layer was re-extracted with DCM (2×150 ml)
  4. dry with materialdried (MgSO4)
  5. customthe resulting clear oil was purified by column chromatography on silica gel EtOAc/iso-Hexane (2:8)

Sources & evidence

ORD record
ord-06e1be2bc3484e199a0a8edaa3f7168b
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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