Dimethylformamide → 1-Ethyl-3-(4-(7-(5-methylpyrazine-2-carbonyl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea

HRID 1698018Notes

Reaction equation

HRID 1698018 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.CN(C)C=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.[CH2:47]([NH:49][C:50]([NH:52][C:53]1[CH:58]=[CH:57][C:56]([C:59]2[N:60]=[C:61]([N:69]3[CH2:74][CH2:73][O:72][CH2:71][CH2:70]3)[C:62]3[CH2:68][CH2:67][NH:66][CH2:65][C:63]=3[N:64]=2)=[CH:55][CH:54]=1)=[O:51])[CH3:48]>>[CH2:47]([NH:49][C:50]([NH:52][C:53]1[CH:54]=[CH:55][C:56]([C:59]2[N:60]=[C:61]([N:69]3[CH2:70][CH2:71][O:72][CH2:73][CH2:74]3)[C:62]3[CH2:68][CH2:67][N:66]([C:8]([C:5]4[CH:4]=[N:3][C:2]([CH3:1])=[CH:7][N:6]=4)=[O:10])[CH2:65][C:63]=3[N:64]=2)=[CH:57][CH:58]=1)=[O:51])[CH3:48]

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1228315-Methyl-2-pyrazinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Product 1

HCID 592392551-Ethyl-3-(4-(7-(5-methylpyrazine-2-carbonyl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea

Procedure

5-Methylpyrazine-2-carboxylic acid (0.0490 g, 0.000355 mol) in dry N,N-Dimethylformamide (1.80 mL, 0.0232 mol) was added 1-Hydroxybenzotriazole (0.0547 g, 0.000405 mol) followed by N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.0797 g, 0.000416 mol) then followed by N,N-Diisopropylethylamine (0.114 mL, 0.000654 mol) and then 1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.1007 g, 0.0002633 mol). The reaction mixture was stirred overnight. The reaction mixture was vacuum filtered, washed with DMF and then washed with water. 1H NMR (400 MHz, DMSO) δ 8.81 (d, J=3.3, 1H), 8.64 (d, J=12.5, 2H), 8.26-8.10 (m, 2H), 7.47 (dd, J=18.5, 8.7, 2H), 6.15 (dd, J=13.1, 5.8, 1H), 4.74 (d, J=15.5, 2H), 3.87 (s, 1H), 3.71 (dd, J=14.7, 4.6, 5H), 3.48 (d, J=3.9, 4H), 3.18-3.03 (m, 2H), 2.75 (d, J=13.1, 2H), 2.59 (s, 3H), 1.06 (dd, J=12.5, 7.1, 3H). LC/MS-m/z+503.2 (M+H)+,

Workup

  1. filtrationfiltered
  2. washwashed with DMF
  3. washwashed with water

Sources & evidence

ORD record
ord-0cbc9dba22c54294a2375002e8f139a8
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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