Water → HCID 59639515, compound

HRID 2249743Notes

Reaction equation

HRID 2249743 reaction equation
CS([C:5]1[N:6]=[C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:8]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[N:10]=1)(=O)=O.CN1C(=O)CCC1.[CH2:35]([N:37]([CH2:41][CH3:42])[CH2:38][CH2:39][NH2:40])[CH3:36].O>CCOC(C)=O>[CH2:35]([N:37]([CH2:41][CH3:42])[CH2:38][CH2:39][NH:40][C:5]1[N:6]=[C:7]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:8]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[N:10]=1)[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 60993N,N-DiethylethylenediamineHCID 59639663HCID 59639663, compound

Product 1

HCID 59639515HCID 59639515, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Example 46 (18.8 mg, 0.05 mmol), NMP (5 mL) and N,N-diethylethylenediamine (28 mg, 0.25 mmol, 5 eq) was heated to 50°. After 1 h, H2O (20 mL) was added and then EtOAc (20 mL). The layers were separated. The organic layer was washed with satd aq NaCl, dried (MgSO4) filtered and the solvent was evaporated in vacuo. The yellow residue was purified by Flash chromatography to afford 2-(2-diethylamino-ethylamino)-4,8-diphenyl-8H-pyrido[2,3-d]pyrimidin-7-one (21 mg, 89% yield). 1H-NMR (CDCl3) δ 0.74-0.98 (m, 6H), 2.28-2.56 (m, 8H), 2.98 (br s, 1H), 6.32 (d, 1H, J=9.8 Hz), 7.26 (m, 2H), 7.09-7.88 (m, 1H), LC MS (m/e)=414 (MH+).

Workup

  1. customThe layers were separated
  2. washThe organic layer was washed with satd aq NaCl
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated in vacuo
  6. customThe yellow residue was purified by Flash chromatography

Sources & evidence

ORD record
ord-c4ee8b9d42344c1eb059d63953608cd7
Source dataset
uspto-grants-2008_01
Patent number
US07314881B2

Reaction notes

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