Triethylamine → HCID 44190035, compound

HRID 40541Notes

Reaction equation

HRID 40541 reaction equation
CS([C:5]1[N:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][N:6]=1)(=O)=O.Cl.CN.C[CH2:23][N:24](CC)CC>C1COCC1>[CH3:23][NH:24][C:5]1[N:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 575167582-Methanesulfonyl-5-phenylethynyl-pyrimidine

Product 1

HCID 44190035HCID 44190035, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

(100 mg, 0.38 mmol) 2-Methanesulfonyl-5-phenylethynyl-pyrimidine (Example 8, step 2), methylamine hydrochloride (52 mg, 0.77 mmol, 2 equiv.) and Et3N (220 μl, 1.55 mmol, 4 equiv.) were suspended in 1 ml THF and stirred for 1 hour at 65° C. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography by directly loading the crude material onto a silica gel column and eluting with (heptane:ethyl acetate 100:0->0:100). The desired methyl-(5-phenylethynyl-pyrimidin-2-yl)-amine was obtained as a white solid (38 mg, 47%), MS: m/e=210.2 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography
  3. washeluting with (heptane:ethyl acetate 100:0->0:100)

Sources & evidence

ORD record
ord-99d3754579e5482b8deefd741b0b2f41
Source dataset
uspto-grants-2013_09
Patent number
US08530472B2

Reaction notes

Loading…