Sodium Methoxide → HCID 70003236, compound

HRID 431829Notes

Reaction equation

HRID 431829 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:12][C@H:11]([S:13][C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][C@H:9]2[CH2:33][O:34][CH2:35][C:36]2[CH:41]=[C:40]([F:42])[C:39]([F:43])=[CH:38][C:37]=2[F:44])[CH:5]=[CH:4][N:3]=1.[CH3:45][O-:46].[Na+]>CO>[CH3:45][O:46][C:2]1[N:7]=[C:6]([N:8]2[CH2:12][C@H:11]([S:13][C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][C@H:9]2[CH2:33][O:34][CH2:35][C:36]2[CH:41]=[C:40]([F:42])[C:39]([F:43])=[CH:38][C:37]=2[F:44])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86585172HCID 86585172, compound

Product 1

HCID 70003236HCID 70003236, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 0.24 (0.4 mmol) (2S,4R)-2-Chloro-4-[2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine in 1 ml MeOH was treated at 0° C. with 0.16 ml (0.88 mmol) sodium methylate (5.5 M in MeOH) and kept at this temperature (2 h), warmed up and heated for 10 h at 75° C. After evaporation and extraction with aqueous saturated NH4Cl/Et2O (3×), the organic phases were washed with aq. 10% NaCl, dried (Na2SO4) and evaporated to give 0.19 g (77%) 2-Methoxy-4-[(2S,4R)-2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine, MS: 628 (MH+), which was deprotected (see General method for S-deprotection, Method D) to give (3R,5S)-1-(2-Methoxy-pyrimidin-4-yl)-5-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-3-thiol, MS: 386 (MH+).

Workup

  1. customkept at this temperature (2 h)
  2. temperaturewarmed up
  3. customAfter evaporation and extraction with aqueous saturated NH4Cl/Et2O (3×)
  4. washthe organic phases were washed with aq. 10% NaCl
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-7c1fbf1aba65475fb6ce33789dfb4039
Source dataset
uspto-grants-2003_12
Patent number
US06660738B2

Reaction notes

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