Triethylamine → HCID 89825596, compound

HRID 2206841Notes

Reaction equation

HRID 2206841 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[Cl-].[CH2:11]([C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[O:19][CH2:18][CH2:17][CH:16]2[NH3+:23])[CH3:12].C(N(CC)CC)C>CN(C)C(=O)C>[CH2:11]([C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[O:19][CH2:18][CH2:17][CH:16]2[NH:23][C:2]1[CH:3]=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1)[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6865465-Bromopyrimidine-2-carbonitrileHCID 89826211HCID 89826211, compound

Product 1

HCID 89825596HCID 89825596, compoundYield 9.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

0.20 g (1.09 mmol) of 5-bromo-2-cyanopyrimidine (ABCR 245244), 0.325 g (1.52 mmol) of 6-ethyl-3,4-dihydro-2H-chromen-4-aminium chloride and 0.35 g (3.3 mmol) of triethylamine in 1.5 ml of N,N-dimethylacetamide are heated in a closed cuvette in the microwave at 200° C. for 120 minutes (Biotage Initiator, http://www.biotage.com/DynPage.aspx?id=22001). The crude mixture obtained in this manner is applied to silica gel and purified by column chromatography using the mobile phase heptane/ethyl acetate. Concentration gives 0.03 g of 5-[(6-ethyl-3,4-dihydro-2H-chromen-4-yl)amino]pyrimidine-2-carbonitrile (wax-like) (yield 8% at a purity of 80%).

Workup

  1. customThe crude mixture obtained in this manner
  2. custompurified by column chromatography
  3. concentrationConcentration

Sources & evidence

ORD record
ord-4c17e9341005488087e5c6c5aa21f9e5
Source dataset
uspto-grants-2016_06
Patent number
US09375002B2

Reaction notes

Loading…