Triethylamine → 4-Cyclopentyl-6-(1-piperazinyl)-2-pyrimidinamine

HRID 2075792Notes

Reaction equation

HRID 2075792 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1.C([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(OC(C)(C)C)=O.CCN(CC)CC>CCO>[CH:9]1([C:4]2[CH:5]=[C:6]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:7]=[C:2]([NH2:1])[N:3]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 218463674-Chloro-6-cyclopentylpyrimidin-2-amine

Product 1

HCID 247981444-Cyclopentyl-6-(1-piperazinyl)-2-pyrimidinamineYield 18.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of crude 2-amino-4-chloro-6-cyclopentylpyrimidine (150 mg, 0.76 mmol), N-BOC piperazine (184 mg, 0.99 mmol) and Et3N (210 uL, 1.5 mmol) in EtOH (2 mL) was heated at 70° C. for 16 h. The reaction was cooled to rt and concentrated and the crude residue purified (2 M NH3 in MeOH/CH2Cl2) to yield a white solid (34 mg, 11%). MS (ESI): mass calcd. for C18H29N5O2, 347.2; m/z found, 348.3 [M+H]+. 1H NMR (MeOD): 6.01 (s, 1H), 3.66-3.58 (m, 4H), 3.53-3.43 (m, 4H), 3.33 (td, J=3.3, 1.6, 1H), 2.90-2.75 (m, 1H), 2.05-1.90 (m, 2H), 1.87-1.77 (m, 2H), 1.77-1.62 (m, 4H), 1.53-1.46 (m, 9H).

Workup

  1. concentrationconcentrated
  2. customthe crude residue purified (2 M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7915622ae4624d508fb4076d5da9a5b1
Source dataset
uspto-grants-2011_04
Patent number
US07923451B2

Reaction notes

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