N-methyl-2-pyrrolidone → HCID 86646094, compound

HRID 1800741Notes

Reaction equation

HRID 1800741 reaction equation
[N+:1]([C:4]1[C:5]([S:26][C:27]#[N:28])=[N:6][C:7]([NH:10][C:11]2[CH:12]=[C:13]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:14]=[CH:15][C:16]=2[CH3:17])=[N:8][CH:9]=1)([O-])=O.CN1CCCC1=O.[Cl-].[Ca+2].[Cl-]>C(O)C>[NH2:28][C:27]1[S:26][C:5]2[N:6]=[C:7]([NH:10][C:11]3[CH:12]=[C:13]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:14]=[CH:15][C:16]=3[CH3:17])[N:8]=[CH:9][C:4]=2[N:1]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 5284359Calcium ChlorideHCID 86646092HCID 86646092, compound

Product 1

HCID 86646094HCID 86646094, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the above-mentioned crude product of tert-butyl {3-[(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]-4-methylphenyl}carbamate in ethanol (120 mL)/1-methylpyrrolidin-2-one (80 mL) were added reduced iron (6.68 g, 120 mmol) and aqueous solution (20 mL) of calcium chloride (13.3 g, 120 mmol), and the mixture was stirred at 100° C. for 16 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. To the obtained residue was added water (350 mL), and the mixture was extracted with ethyl acetate (200 mL, 2×80 mL). The combined organic layer was washed with saturated brine (50 mL), filtered through a silica gel pad, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate to give the title compound (5.24 g, 35%) as a gray solid.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the obtained residue was added water (350 mL)
  4. extractionthe mixture was extracted with ethyl acetate (200 mL, 2×80 mL)
  5. washThe combined organic layer was washed with saturated brine (50 mL)
  6. filtrationfiltered through a silica gel pad
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washThe obtained residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-6f3e1d11e4b049d89842ee9d34f122a2
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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