Water → tert-Butyl 3-carbamothioyl-2-[2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl]pyrrolidine-1-carboxylate

HRID 1170543Notes

Reaction equation

HRID 1170543 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH:24]([C:27](=O)[NH2:28])[CH:23]1[C:30]1[CH:35]=[C:34]([CH3:36])[N:33]=[C:32]([N:37]2[CH:41]=[CH:40][N:39]=[CH:38]2)[N:31]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16].O>C(COC)OC>[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH:24]([C:27](=[S:2])[NH2:28])[CH:23]1[C:30]1[CH:35]=[C:34]([CH3:36])[N:33]=[C:32]([N:37]2[CH:41]=[CH:40][N:39]=[CH:38]2)[N:31]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 58654505HCID 58654505, compound

Product 1

HCID 57355453tert-Butyl 3-carbamothioyl-2-[2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl]pyrrolidine-1-carboxylateYield 95.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

P2S5 (60 mg, 0.27 mmol) was added to a solution of 3-carbamoyl-2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (10 mg, 0.30 mmol) in dimethoxyethane (10 mL) at rt under an atmosphere of N2. The reaction mixture was heated to 100° C. for 2 h then cooled to rt. Water (20 mL) was added and the solution was extracted with DCM (3×30 mL). The combined organics were dried over Na2SO4, filtered and concentrated under vacuum to afford 100 mg (86%) of 2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-3-thiocarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester as a yellow oil.

Workup

  1. temperaturethen cooled to rt
  2. extractionthe solution was extracted with DCM (3×30 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cee301c8787346ffb697922bbb17adac
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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