Dimethylformamide → HCID 59239429, compound

HRID 1698012Notes

Reaction equation

HRID 1698012 reaction equation
ClC1N=C([N:8]2[CH2:17][CH2:16][C:15]3[C:14]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[N:13][C:12]([C:24]4[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][CH2:34][CH3:35])=[O:32])=[CH:26][CH:25]=4)=[N:11][C:10]=3[CH2:9]2)C=C(C)N=1.C(NC(NC1C=CC(C2N=C(N3CCOCC3)C3CCNCC=3N=2)=CC=1)=O)C.Cl[C:66]1[N:71]=[C:70]([Cl:72])[CH:69]=[C:68]([CH3:73])[N:67]=1.CN(C)C=O.C(N(CC)C(C)C)(C)C>>[Cl:72][C:70]1[CH:69]=[C:68]([CH3:73])[N:67]=[C:66]([N:8]2[CH2:17][CH2:16][C:15]3[C:14]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[N:13][C:12]([C:24]4[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][CH2:34][CH3:35])=[O:32])=[CH:26][CH:25]=4)=[N:11][C:10]=3[CH2:9]2)[N:71]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 794712,4-Dichloro-6-methylpyrimidineHCID 81531DiisopropylethylamineHCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)ureaHCID 59239646HCID 59239646, compound

Product 1

HCID 59239429HCID 59239429, compound

Procedure

and 1-(4-(7-(2-chloro-6-methylpyrimidin-4-yl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea (vz2): 1-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0506 g, 0.132 mmol) and 2,4-Dichloro-6-methylpyrimidine (0.0360 g, 0.221 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 concentrated, chromatographed through silica gel (4 g, 0-100% EtOAc in heptane), and then purified by HPLC. 1-(4-(7-(4-chloro-6-methylpyrimidin-2-yl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea (vz1): 1H NMR (500 MHz, DMSO) δ 8.62 (s, 1H), 8.21 (d, J=8.8, 2H), 7.49 (d, J=8.8, 2H), 6.71 (s, 1H), 6.15 (t, J=5.6, 1H), 4.81 (s, 2H), 3.96 (s, 2H), 3.78-3.68 (m, 4H), 3.53-3.41 (m, 4H), 3.17-3.05 (m, 2H), 2.75 (t, J=5.2, 2H), 2.34 (s, 3H), 1.07 (t, J=7.2, 3H). LC/MS-m/z+509.2 (M+H)+; 1-(4-(7-(2-chloro-6-methylpyrimidin-4-yl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea (vz2): 1H NMR (500 MHz, DMSO) δ 8.63 (s, 1H), 8.21 (d, J=8.8, 2H), 7.49 (d, J=8.8, 2H), 6.88 (s, 1H), 6.16 (t, J=5.6, 1H), 4.69 (s, 2H), 3.86 (s, 2H), 3.78-3.69 (m, 4H), 3.56-3.43 (m, 4H), 3.18-3.04 (m, 2H), 2.77 (d, J=4.6, 2H), 2.29 (s, 3H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+509.2 (M+H)+

Workup

  1. customThe reaction was microwaved on 200 watts, 120° C. for 30 minutes on a CEM microwave
  2. concentrationThe reaction mixture was concentrated
  3. customchromatographed through silica gel (4 g, 0-100% EtOAc in heptane)
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-fab6588551c64d52ab7813ea0727d7c1
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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