Hydrochloric Acid → (R)-8-cyclopentyl-7-ethyl-2-(4-iminopyridin-1(4H)-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one

HRID 44842

Reaction equation

Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C@@H:6]([CH2:14][CH3:15])[N:5]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:4]=2[N:3]=1.Cl.[NH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1>C(O)(C)C.O1CCOCC1>[CH:16]1([N:5]2[C:4]3[N:3]=[C:2]([N:26]4[CH:27]=[CH:28][C:23](=[NH:22])[CH:24]=[CH:25]4)[N:11]=[CH:10][C:9]=3[N:8]([CH3:12])[C:7](=[O:13])[C@H:6]2[CH2:14][CH3:15])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of the Intermediate B (400 mg, 1.36 mmol) in 5 mL of isopropanol in a microwave vial, 4N HCl in dioxane (0.43 mL) and 4-aminopyridine (320 mg, 2 eq) were added and the vial was heated in a microwave oven at 160° C. for 1 hour. Solvent was removed under reduced pressure and the resulting yellow solid was purified by reversed phase HPLC to give the title compound. 1H NMR (CDCl3) δ: 9.62 (bs, 1H), 8.91 (d, J=7.7 Hz, 2H), 7.81 (s, 1H), 7.37 (d, J=7.8 Hz, 2H), 4.44-4.36 (m, 2H), 3.41 (s, 3H), 2.08-1.71 (m, 10H), 0.89 (t, J=7.5 Hz, 3H).

Workup

customSolvent was removed under reduced pressure
customthe resulting yellow solid was purified by reversed phase HPLC

Sources & evidence

ORD record: ord-782895ef5b6a41cd94753079943b5a3f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541418B2

Linked notes

Loading…