Dimethylformamide → 1-(4-(7-(3-Chloropyrazin-2-yl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea

HRID 1698003Notes

Reaction equation

HRID 1698003 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].[Cl:29][C:30]1[C:35](Cl)=[N:34][CH:33]=[CH:32][N:31]=1.CN(C)C=O.C(N(CC)C(C)C)(C)C>>[Cl:29][C:30]1[C:35]([N:20]2[CH2:21][CH2:22][C:16]3[C:15]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[N:14][C:13]([C:10]4[CH:9]=[CH:8][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:12][CH:11]=4)=[N:18][C:17]=3[CH2:19]2)=[N:34][CH:33]=[CH:32][N:31]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 785752,3-DichloropyrazineHCID 81531DiisopropylethylamineHCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Product 1

HCID 592394201-(4-(7-(3-Chloropyrazin-2-yl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea

Procedure

1-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0496 g, 0.130 mmol) and 2,3-Dichloropyrazine (0.0204 mL, 0.196 mmol) were combined then added dry N,N-Dimethylformamide (0.910 mL, 11.8 mmol) followed by N,N-Diisopropylethylamine (0.0456 mL, 0.262 mmol). The reaction was microwaved on 200 watts, 120° C. for 30 minutes on a CEM microwave. The reaction mixture was purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.64 (s, 1H), 8.30 (d, J=2.5, 1H), 8.21 (d, J=8.8, 2H), 8.01 (d, J=2.5, 1 H), 7.49 (d, J=8.8, 2H), 6.15 (t, J=5.6, 1H), 4.55 (d, J=15.7, 2H), 3.82-3.63 (m, 6H), 3.56-3.45 (m, 4H), 3.17-3.07 (m, 2H), 2.86 (s, 2H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+495.2 (M+H)+.

Workup

  1. customThe reaction was microwaved on 200 watts, 120° C. for 30 minutes on a CEM microwave
  2. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-139dd4f5cbc643c99088021054b48b73
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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