Diisopropylethylamine → HCID 67540451, compound

HRID 1192342Notes

Reaction equation

HRID 1192342 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].CCN(C(C)C)C(C)C>CC(O)C>[C:11]([N:18]1[CH2:19][CH2:20][N:21]([C:6]2[N:7]=[CH:2][C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=2)[CH2:22][CH2:23]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 67540451HCID 67540451, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution containing 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (5.0 g, 32.6 mmol), Boc-piperazine (15 g, 81 mmol), and DIEA (19.8 mL, 114 mmol) in 130 mL IPA was stirred at 80 C for 18 hours, after which the reaction was concentrated. The crude was flashed on silica gel (20:1 DCM:MeOH) to give a yellow powder, which was recrystallized from MeOH/minimal DCM to give 4-Boc-piperazin-1-yl-7H-pyrrolo[2,3-d]pyrimidine as a white crystalline solid (3 crops). 1H NMR (CDCl3, 400 MHz) δ 11.37 (br s, 1H), 8.34 (s, 1H), 7.12 (d, J=3.3 Hz, 1H), 6.49 (d, J=3.5 Hz, 1H), 4.01-3.94 (m, 4H), 3.64-3.56 (m, 4H), 1.48 (s, 9H). HPLC Rt 2.05 min.

Workup

  1. concentrationafter which the reaction was concentrated
  2. customto give a yellow powder, which
  3. customwas recrystallized from MeOH/minimal DCM

Sources & evidence

ORD record
ord-20b12c98b4e6426f9196effe98819eb4
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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