Sodium methanethiolate → HCID 59178898, compound

HRID 1947662Notes

Reaction equation

HRID 1947662 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:3]=1.[CH3:27][S-:28].[Na+]>CN1C(=O)CCC1.C(OCC)(=O)C>[CH3:27][S:28][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:3]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 59178818HCID 59178818, compound

Product 1

HCID 59178898HCID 59178898, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The tert-butyl 1′-(6-chloropyrimidin-4-yl)-4,4′-bipiperidine-1-carboxylate (100 mg, 0.26 mmol) was dissolved in NMP (2.6 mL), and sodium methanethiolate (18.2 mg, 0.26 mmol) was added. The reaction was stirred at r.t. for 30 min. The reaction crude was diluted with ethyl acetate (10 mL) and was washed with water (10 mL, ×1) and brine (10 mL, ×1), dried over magnesium sulfate, filtered and concentrated by rotavapor. The crude mixture was purified by preparative TLC with 30% ethylacetate:hexane to yield the title compound.

Workup

  1. customThe reaction crude
  2. washwas washed with water (10 mL, ×1) and brine (10 mL, ×1)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotavapor
  6. customThe crude mixture was purified by preparative TLC with 30% ethylacetate

Sources & evidence

ORD record
ord-f4e580571197461fb59b013fc375541e
Source dataset
uspto-grants-2013_03
Patent number
US08399485B2

Reaction notes

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