Dimethylformamide → HCID 44815761, compound

HRID 1697999Notes

Reaction equation

HRID 1697999 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.[H-].[Na+].Cl[C:37]1[CH:42]=[C:41]([CH3:43])[N:40]=[CH:39][N:38]=1>>[CH2:1]([NH:3][C:4]([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:37]4[CH:42]=[C:41]([CH3:43])[N:40]=[CH:39][N:38]=4)[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydride2×HCID 5817964-Chloro-6-methylpyrimidineHCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Product 1

HCID 44815761HCID 44815761, compound

Conditions

Temperature
60 °C

Procedure

1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0499 g, 0.000130 mol) in dry N,N-Dimethylformamide (1.00 mL, 0.0129 mol) was cooled at 0° C. then added sodium hydride, 60% dispension in mineral oil (3:2, Sodium hydride:Mineral Oil, 0.0109 g), warmed to room temperature, stirred for 10 minutes, added 4-Chloro-6-methylpyrimidine (0.0196 g, 0.000152 mol) heated at 60° C. for 3 hours. LC-MS does show some product present but a lot of starting material is still remaining. The reaction mixture was heated at 60° C. and stirred overnight. The reaction mixture was filtered and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.64 (s, 1H), 8.44 (s, 1H), 8.21 (d, J=8.8, 2H), 7.49 (d, J=8.8, 2H), 6.86 (s, 1H), 6.16 (t, J=5.6, 1H), 4.69 (s, 2H), 3.87 (s, 2H), 3.79-3.68 (m, 4H), 3.48 (d, J=4.4, 4H), 3.20-3.05 (m, 2H), 2.75 (s, 2H), 2.30 (s, 3H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+475.3 (M+H)+

Workup

  1. temperatureThe reaction mixture was heated at 60° C.
  2. stirringstirred overnight
  3. filtrationThe reaction mixture was filtered
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-642606985ee94025ad255cc1d75c5c22
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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