Dimethylformamide → HCID 59239390, compound

HRID 1698016Notes

Reaction equation

HRID 1698016 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][C@@H:24]3[CH3:29])[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:30][C:31]1[CH:36]=[C:35](Cl)[N:34]=[CH:33][N:32]=1.CN(C)C=O>>[Cl:30][C:31]1[N:32]=[CH:33][N:34]=[C:35]([N:20]2[CH2:21][CH2:22][C:16]3[C:15]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]4[CH3:29])=[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)[CH:36]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 709434,6-DichloropyrimidineHCID 46913570Urea, N-ethyl-N'-[4-[5,6,7,8-tetrahydro-4-[(3S)-3-Methyl-4-Morpholinyl]pyrido[3,4-d]pyriMidin-2-yl]phenyl]-

Product 1

HCID 59239390HCID 59239390, compound

Procedure

(S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.196 g, 0.376 mmol), 4,6-dichloropyrimidine (0.112 g, 0.752 mmol) N,N-Diisopropylethylamine (0.150 mL, 0.861 mmol) and dry N,N-Dimethylformamide (1.1 mL, 14 mmol) were combined, The reaction was microwaved on 200 watts, 120° C. for 20 minutes on a CEM microwave. The reaction mixture was concentrated and chromatographed through silica gel (40 g, 0-10% MeOH in dichloromethane), and purified by HPLC. 1H NMR (500 MHz, DMSO) δ 8.69 (s, 1H), 8.41 (s, 1H), 8.20 (d, J=8.7, 2H), 7.50 (d, J=8.7, 2H), 7.12 (s, 1H), 6.20 (t, J=5.6, 1H), 4.72 (s, 3H), 4.12 (s, 1H), 4.08-3.92 (m, 1H), 3.88 (d, J=9.4, 1H), 3.80 (s, 1H), 3.64 (dt, J=25.7, 10.3, 4H), 3.43 (t, J=12.6, 1H), 3.17-3.04 (m, 2H), 2.75 (s, 2H), 1.26 (d, J=6.7, 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 20 minutes on a CEM microwave
  2. concentrationThe reaction mixture was concentrated
  3. customchromatographed through silica gel (40 g, 0-10% MeOH in dichloromethane)
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-7dd1ccf716f44177bf7de595a2ee5bba
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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