Triethylamine → HCID 59333680, compound

HRID 421344Notes

Reaction equation

HRID 421344 reaction equation
Cl[C:2]1[N:3]([CH2:25][CH:26]2[CH2:28][CH2:27]2)[C:4]2[C:9]([N:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[N:7]=[C:6]([C:17]1[C:18]([CH3:24])=[N:19][C:20]([NH2:23])=[N:21][CH:22]=1)[N:5]=2.[NH2:29][CH:30]1[CH2:34][CH2:33][NH:32][CH2:31]1.C(N(CC)CC)C.[S:42](Cl)([CH3:45])(=[O:44])=[O:43]>CN1CCCC1=O>[NH2:23][C:20]1[N:19]=[C:18]([CH3:24])[C:17]([C:6]2[N:5]=[C:4]3[C:9]([N:10]=[C:2]([N:32]4[CH2:33][CH2:34][CH:30]([NH:29][S:42]([CH3:45])(=[O:44])=[O:43])[CH2:31]4)[N:3]3[CH2:25][CH:26]3[CH2:28][CH2:27]3)=[C:8]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[N:7]=2)=[CH:22][N:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1644013-AminopyrrolidineHCID 59333498HCID 59333498, compound

Product 1

HCID 59333680HCID 59333680, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

N-Methylpyrrolidone (1 ml) was added to 5-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]-4-methylpyrimidin-2-amine (100 mg, 0.25 mmol) and 3-aminopyrrolidine (130 mg, 1.5 mmol) and the resulting mixture was stirred at 120° C. for 1 hour. The reaction mixture was partitioned with chloroform and saturated brine and the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was concentrated under reduced pressure, then triethylamine (100 μl, 0.75 mmol) and mesyl chloride (60 μl, 0.75 mmol) were added to the residue, and the resulting mixture was stirred for 1 hour. The reaction mixture was partitioned with ethyl acetate and water and the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid) to give the title compound (70 mg, 53%) as a pale yellow solid.

Workup

  1. customThe reaction mixture was partitioned with chloroform and saturated brine
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. stirringthe resulting mixture was stirred for 1 hour
  6. customThe reaction mixture was partitioned with ethyl acetate and water
  7. washthe organic layer was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid)

Sources & evidence

ORD record
ord-7c60b95c93d84c25918fc4c288e24820
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

Loading…