Dimethylformamide → isobutyl 2-(4-(3-ethylureido)phenyl)-4-morpholino-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

HRID 1697998Notes

Reaction equation

HRID 1697998 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:16]3[CH2:22][CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].CN(C)C=O.C(N(CC)C(C)C)(C)C.Cl[C:44]([O:46][CH2:47][CH:48]([CH3:50])[CH3:49])=[O:45]>>[CH2:1]([NH:3][C:4](=[O:5])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[C:16]3[CH2:22][CH2:21][N:20]([C:44]([O:46][CH2:47][CH:48]([CH3:50])[CH3:49])=[O:45])[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Product 1

HCID 59239184isobutyl 2-(4-(3-ethylureido)phenyl)-4-morpholino-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

Procedure

1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea (0.0867 g, 0.227 mmol) in dry N,N-Dimethylformamide (1.00 mL, 12.9 mmol) at 0° C. was added N,N-Diisopropylethylamine (0.1190 mL, 0.6832 mmol) followed by Isobutyl chloroformate (0.0442 mL, 0.341 mmol). The reaction mixture was allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was concentrated and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.67 (s, 1H), 8.18 (d, J=8.8, 2H), 7.48 (d, J=8.8, 2H), 6.18 (t, J=5.6, 1H), 4.52 (s, 2H), 3.86 (d, J=6.5, 2H), 3.77-3.68 (m, 4 H), 3.58 (s, 2H), 3.47 (d, J=4.3, 4H), 3.17-3.06 (m, 2H), 2.73-2.62 (m, 2H), 1.92 (dp, J=13.2, 6.6, 1H), 1.06 (t, J=7.2, 3H), 0.93 (d, J=6.7, 6H). LC/MS-m/z+483.3 (M+H)+

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-0026ea2ad8d84a0fa1bbbef7c5345571
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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