Triethylamine → HCID 59333667, compound

HRID 1876533Notes

Reaction equation

HRID 1876533 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.[CH3:29][NH:30][CH:31]1[CH2:35][CH2:34][NH:33][CH2:32]1.C(N(CC)CC)C.[S:43](Cl)([CH3:46])(=[O:45])=[O:44]>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:33]4[CH2:34][CH2:35][CH:31]([N:30]([CH3:29])[S:43]([CH3:46])(=[O:45])=[O:44])[CH2:32]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 117882683-(Methylamino)pyrrolidineHCID 59333498HCID 59333498, compound

Product 1

HCID 59333667HCID 59333667, compoundYield 55.3%

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-methylaminopyrrolidine (130 mg, 1.5 mmol) and the resulting mixture was stirred at 120° C. for 0.5 hours. 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, 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 (containing a small amount of tetrahydrofuran) 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 silica gel chromatography (chloroform:methanol=9:1) to give a pale yellow solid (75 mg, 50%).

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. additionwere added to the residue
  5. stirringthe resulting mixture was stirred for 1 hour
  6. customThe reaction mixture was partitioned with ethyl acetate (
  7. additioncontaining a small amount of tetrahydrofuran) and water
  8. washthe organic layer was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe residue was purified by silica gel chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-8e24855e079242c6986d2330f635c2b6
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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