Diisopropylethylamine → HCID 89812826, compound

HRID 717103Notes

Reaction equation

HRID 717103 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH:42]1([CH2:45][N:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[CH2:44][CH2:43]1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]([C:8]([N:49]2[CH2:50][CH2:51][N:46]([CH2:45][CH:42]3[CH2:44][CH2:43]3)[CH2:47][CH2:48]2)=[O:10])=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9658751-(Cyclopropylmethyl)piperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 164629705-Bromopyrimidine-2-carboxylic acid

Product 1

HCID 89812826HCID 89812826, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 5-bromopyrimidine-2-carboxylic acid (100 mg, 0.49 mmol) and TBTU (158 mg, 0.49 mmol) in anhydrous DMF 94.4. mL) was added DIPEA (0.36M in CH2Cl2, 1.4 mL, 0.49 mmol) and the reaction mixture stirred at RT for 40 min. N-cyclopropylmethylpiperazine (83 mg, 0.59 mmol) in anhydrous DMF (1 mL) was added and the reaction stirred at RT for 18 h. The reaction mixture was passed through a Si—NH2 cartridge (5 g), eluting with DMF and MeOH. The eluents were combined, concentrated in vacuo and purified by reverse phase preparative HPLC-MS to obtain (5-bromo-pyrimidin-2-yl)-(4-cyclopropylmethyl-piperazin-1-yl)-methanone as a pale yellow solid (46 mg, 29%).

Workup

  1. stirringthe reaction stirred at RT for 18 h
  2. washeluting with DMF and MeOH
  3. concentrationconcentrated in vacuo
  4. custompurified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-5e3ef2d228734defbfa9e748caec6d05
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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