Diisopropylethylamine → HCID 178456856, compound

HRID 58228Notes

Reaction equation

HRID 58228 reaction equation
Br[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[NH2:11][CH:12]([C:15]1[N:16]=[C:17]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:18]2[C:19](=[O:27])[C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:13][CH3:14].C(N(CC)C(C)C)(C)C>C(O)C>[CH3:32][C:28]1[N:18]2[C:19](=[O:27])[C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[C:15]([CH:12]([NH:11][C:2]3[N:10]=[CH:9][N:8]=[C:7]4[C:3]=3[N:4]=[CH:5][NH:6]4)[CH2:13][CH3:14])[N:16]=[C:17]2[CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 668636882-(1-aminopropyl)-6-methyl-3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 178419477HCID 178419477, compound

Product 1

HCID 178456856HCID 178456856, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-bromo-9H-purine (Aldrich, 0.0152 g, 0.07656 mmol), 2-(1-aminopropyl)-6-methyl-3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one (0.019 g, 0.064 mmol), and N,N-diisopropylethylamine (0.0134 mL, 0.07666 mmol) in ethanol (0.5 mL) was refluxed under nitrogen overnight. The mixture was cooled and purified on RP-HPLC at pH 10 (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.15% NH4OH) to provide the product as the free base. LCMS calculated for C23H22N7O (M+H)+: m/z=412.2. Found: 412.4. 1H NMR (DMSO-d6, 300 MHz) δ 8.07 (2H, m), 7.60 (1H, dd, J=9.0 and 6.9 Hz), 7.39-7.32 (7H, m), 7.00 (1H, m), 6.85 (1H, br d, J=6.9 Hz), 5.13 (1H, m), 2.81 (3H, s), 1.72 (2H, m), 0.65 (3H, t, J=7.2 Hz) ppm.

Workup

  1. temperaturewas refluxed under nitrogen overnight
  2. temperatureThe mixture was cooled
  3. custompurified on RP-HPLC at pH 10 (XBridge C18 column
  4. washeluting with a gradient of acetonitrile/water containing 0.15% NH4OH)
  5. customto provide the product as the free base

Sources & evidence

ORD record
ord-625cadb4afd74544805639870b86dafb
Source dataset
uspto-grants-2016_09
Patent number
US09434746B2

Reaction notes

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