Triethylamine → HCID 42610708, compound

HRID 384627Notes

Reaction equation

HRID 384627 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=2)[CH:3]=1.[NH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(N(CC)CC)C>CC#N>[O:22]1[CH2:23][CH2:24][CH:19]([CH2:18][NH:17][C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[N:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=3)[CH:3]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27732104-AminomethyltetrahydropyranHCID 56926364HCID 56926364, compound

Product 1

HCID 42610708HCID 42610708, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-(6-chloropyrimidin-4-ylamino)pyrazine-2-carbonitrile (20 mg, 0.086 mmol), 4-(aminomethyl)tetrahydropyran (18 mg, 0.17 mmol), and triethylamine (0.02 mL, 0.13 mmol) in MeCN (0.2 mL) was heated to 145° C. for 30 minutes by microwave irradiation. The mixture was cooled and solvent was removed by evaporation. The crude material was redissolved in a mixture of dichloromethane (89%), MeOH (10%), 0.88 s.g. NH3 (1%) and adsorbed onto a solvent-conditioned Trikonex silica chromatography column. Elution with the same solvent mixture gave 5-(6-((tetrahydro-2H-pyran-4-yl)methylamino) pyrimidin-4-ylamino)pyrazine-2-carbonitrile as a yellow powder (11 mg, 41%).

Workup

  1. temperatureThe mixture was cooled
  2. customsolvent was removed by evaporation
  3. dissolutionThe crude material was redissolved in a mixture of dichloromethane (89%), MeOH (10%), 0.88 s
  4. washElution with the same solvent mixture

Sources & evidence

ORD record
ord-726a8225faf84ab2bf7536648aed3da9
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

Loading…