Sodium Iodide → HCID 24751514, compound

HRID 1713110Notes

Reaction equation

HRID 1713110 reaction equation
[N:1]1([C:7]2[N:8]=[CH:9][C:10]3[CH2:16][NH:15][CH2:14][CH2:13][C:11]=3[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[CH:18]1[CH2:23][N:22]([CH:24]2[CH2:27][CH2:26][CH2:25]2)[CH2:21][CH2:20][NH:19]1.[C:28](N)(=[O:30])[CH3:29].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.O>[CH:24]1([N:22]2[CH2:21][CH2:20][N:19]([C:28](=[O:30])[CH2:29][N:15]3[CH2:14][CH2:13][C:11]4[N:12]=[C:7]([N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)[N:8]=[CH:9][C:10]=4[CH2:16]3)[CH2:18][CH2:23]2)[CH2:27][CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 16228818HCID 16228818, compoundHCID 668779022-Chloro-(4-cyclobutyl-piperazine) acetamide

Product 1

HCID 24751514HCID 24751514, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
35 °C

Procedure

To a stirred solution of 2-morpholin-4-yl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine (220 mg, 1.0 mmol) in acetonitrile (5.0 ml) is added 2-chloro-(4-cyclobutyl-piperazine)-acetamide (216 mg, 1.0 mmol, 1.0 eq.), K2CO3 (276 mg, 2.0 mmol, 2.0 eq.) and NaI (50 mg). The resulting mixture is stirred at 35° C. overnight. Water (10.0 ml) is added to quench the reaction, and the acetonitrile is evaporated. The residue is extracted with DCM (10 ml×3), and the combined organic phase is dried over sodium sulfate and concentrated. The residue is purified by preparative silica gel flash chromatography (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.99 (1H, s), 3.75 (8H, s), 3.63 (4H, m), 3.54 (2H, s), 3.36 (2H, s), 2.81 (4H, m), 2.67 (1H, m), 2.27 (4H, m), 1.64˜2.07 (6H, m); MS (+VE) m/z 401.2 (M++1).

Workup

  1. customto quench
  2. customthe reaction
  3. customthe acetonitrile is evaporated
  4. extractionThe residue is extracted with DCM (10 ml×3)
  5. dry with materialthe combined organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is purified by preparative silica gel flash chromatography (EtOAc/4% TEA)

Sources & evidence

ORD record
ord-db2ccf7051e2450891e735f800c1e9d6
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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