Potassium Carbonate → HCID 61961369, compound

HRID 1989078Notes

Reaction equation

[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[NH2:8].[CH2:9]([O:11][C:12]([C:14]1C(Cl)=NC(SC)=N[CH:19]=1)=[O:13])[CH3:10].C([O-])([O-])=O.[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:9]([O:11][C:12](=[O:13])[CH2:14][CH2:19][NH:8][CH:2]1[CH2:3][CH:4]2[CH2:7][CH:1]1[CH2:6][CH2:5]2)[CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

Bicyclo[2.2.1]hept-2-ylamine (2.0 g, 18.0 mmol) and 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (2.45 g, 18.0 mmol) were combined neat and K2CO3 (3.72 g, 27.0 mmol) and a catalytic amount of tetrabutylammonium iodide (ca. 2 mg) was added. The mixture was heated at 80° C. overnight. The resulting mixture was then partitioned between water and DCM. The organic layer was dried (MgSO4) and concentrated to provide 1.5 g of 3-(bicyclo[2.2.1]hept-2-ylamino)-propionic acid ethyl ester. 1H NMR (400 MHz, CDCl3) δ (ppm): 5.29 (s, 1H), 4.13 (q, 2H, J=7.1 Hz), 2.77-2.92 (m, 2H), 2.57 (dd, 1H, J=3.1 Hz, J=7.3 Hz), 2.50 (t, 2H, J=6.6 Hz), 2.16-2.20 (m, 2H), 1.57 (ddd, 1H, J=2.2 Hz, J=7.5 Hz, J=12.3 Hz), 1.41-1.49 (m, 3H), 1.25 (t, 3H, J=7.2 Hz), 1.01-1.10 (m, 4H).

Workup

customThe resulting mixture was then partitioned between water and DCM
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-9e059e44d9f44f859aa8736d8c20f497
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642270B2

Reaction notes

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