Pyridine → N-(2-(3,4-dihydroisoquinolin-2(1H)-yl)-4,6-dimethoxypyrimidin-5-yl)-3,3-dimethylbutanamide

HRID 383710Notes

Reaction equation

HRID 383710 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11]1[N:16]=[C:15]([O:17][CH3:18])[C:14]([NH2:19])=[C:13]([O:20][CH3:21])[N:12]=1.N1C=CC=CC=1.[C:28]([CH2:32][C:33](Cl)=[O:34])([CH3:31])([CH3:30])[CH3:29]>ClCCl>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11]1[N:16]=[C:15]([O:17][CH3:18])[C:14]([NH:19][C:33](=[O:34])[CH2:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:13]([O:20][CH3:21])[N:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 815143,3-Dimethylbutanoyl chlorideHCID 598688212-(3,4-dihydroisoquinolin-2(1H)-yl)-4,6-dimethoxypyrimidin-5-amine

Product 1

HCID 59868733N-(2-(3,4-dihydroisoquinolin-2(1H)-yl)-4,6-dimethoxypyrimidin-5-yl)-3,3-dimethylbutanamideYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4c (0.219 g, 0.76 mmol) and pyridine (0.06 g, 0.76 mmol) in dichloromethane (5 ml) was added tert-butylacetyl chloride (0.102 g, 0.76 mmol). The mixture was stirred at room temperature for 1 hour. The mixture was washed with brine and extracted with ethyl acetate. The organic layer was dried over MgSO4, concentrated and chromatographed to yield the title compound (0.262 g, 0.73 mmol, 96%). 1H NMR (CDCl3, 400 MHz) δ 1.10 (s, 9H), 2.20 (s, 2H), 2.90 (t, J=5.8 Hz, 2H), 3.92 (s, 6H), 4.01 (t, J=5.8 Hz, 2H), 4.87 (s, 2H), 6.14 (s, 1H), 7.15-7.19 (m, 4H).

Workup

  1. washThe mixture was washed with brine
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed

Sources & evidence

ORD record
ord-db77ddb0fc204502beee0bfba10c0d68
Source dataset
uspto-grants-2013_02
Patent number
US08367684B2

Reaction notes

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