1-Methylpiperazine → HCID 24995260, compound

HRID 1962217Notes

Reaction equation

HRID 1962217 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=O)[CH:5]=[C:4]([CH2:9][O:10][CH:11]([CH3:13])[CH3:12])[N:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C1CCN2C(=NCCC2)CC1.[CH3:52][N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1>C(#N)C>[CH:11]([O:10][CH2:9][C:4]1[CH:5]=[C:6]([N:56]2[CH2:57][CH2:58][N:53]([CH3:52])[CH2:54][CH2:55]2)[N:7]=[C:2]([NH2:1])[N:3]=1)([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 136380149HCID 136380149, compound

Product 1

HCID 24995260HCID 24995260, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-amino-6-isopropoxymethyl-3H-pyrimidin-4-one (0.050 g, 0.27 mmol) in acetonitrile (2.37 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.157 g, 0.355 mmol), DBU (0.82 mL, 0.55 mmol), and 1-methyl-piperazine (0.091 ml, 0.82 mmol). The reaction mixture was stirred at rt for 12 h, then at 60° C. for 3 h. The mixture was concentrated and the resultant residue was purified (2 M NH3 in MeOH/CH2Cl2) to yield a white solid (10 mg, 14%). MS (ESI): mass calcd. for C13H23N5O, 265.4; m/z found, 266.3 [M+H]+. 1H NMR (MeOD): 6.55 (s, 1H), 4.49 (s, 2H), 3.78 (quintet, J=6.1, 1H), 3.70-3.00 (m, 8H), 2.95 (s, 3H), 1.25 (d, J=6.1, 6H).

Workup

  1. waitat 60° C. for 3 h
  2. concentrationThe mixture was concentrated
  3. customthe resultant residue was purified (2 M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-5b68c65e764d4bdb90c01ea3ebd6da8a
Source dataset
uspto-grants-2013_04
Patent number
US08415366B2

Reaction notes

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