N-methyl-2-pyrrolidone → HCID 58629084, compound

HRID 1678049Notes

Reaction equation

HRID 1678049 reaction equation
Br[C:2]1[C:10]2[C:9]([NH:11][CH:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1.[CH3:22][N:23]1CCCC1=O>>[C:22]([C:2]1[C:10]2[C:9]([NH:11][CH:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1)#[N:23]

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 67309236HCID 67309236, compound

Product 1

HCID 58629084HCID 58629084, compoundYield 30%

Conditions

Temperature
130 °C

Procedure

5-Bromo-N-[1-(4-methoxyphenyl)ethyl]thieno[2,3-d]pyrimidin-4-amine (250 mg, 0.69 mmol) and cuprous cyanide (310 mg, 3.4 mmol, 5 eq.) were combined in dry N-methylpyrrolidinone (NMP) (4 mL) and heated to 130° C. for 19 hours. After cooling, the volatiles were removed by Kugelrohr distillation at 0.1 mm and the residue was taken up in EtOAc/2 molar NH4OH. The organic phase was washed with water, brine, dried (Na2SO4) and evaporated. The residue was chromatographed on a 50 mm×250 mm YMC-AQ RP HPLC column eluting with 70 percent acetonitrile (ACN) to give 61 mg (30 percent) of the purified off-white solid.

Workup

  1. temperatureAfter cooling
  2. customthe volatiles were removed by Kugelrohr distillation at 0.1 mm
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed on a 50 mm×250 mm YMC-AQ RP HPLC column
  7. washeluting with 70 percent acetonitrile (ACN)

Sources & evidence

ORD record
ord-9804189b58d64e1794bd7d2ac3063b87
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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