Diisopropylethylamine → Methyl 2-(3-(methoxymethyl)piperazin-1-yl)pyrimidine-5-carboxylate

HRID 16872

Reaction equation

HRID 16872 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=1.[CH3:12][O:13][CH2:14][CH:15]1[CH2:20][NH:19][CH2:18][CH2:17][NH:16]1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH3:12][O:13][CH2:14][CH:15]1[NH:16][CH2:17][CH2:18][N:19]([C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=2)[CH2:20]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12627752Methyl 2-chloropyrimidine-5-carboxylateHCID 142302642-(Methoxymethyl)piperazine

Product 1

HCID 66589940Methyl 2-(3-(methoxymethyl)piperazin-1-yl)pyrimidine-5-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl 2-chloropyrimidine-5-carboxylate (300 mg, 1.74 mmol) in DCM (4.70 mL) was added to a stirred solution of 2-(methoxymethyl)piperazine (226 mg, 1.74 mmol) and N-ethyl-N-propan-2-ylpropan-2-amine (0.752 mL, 4.35 mmol) in DCM (4.00 mL) at 25° C. under nitrogen. The resulting solution was stirred at room temperature for 6 h. The reaction mixture was concentrated and diluted with MeOH. The resulting mixture was filtered. The filtrate was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford methyl 2-(3-(methoxymethyl)piperazin-1-yl)pyrimidine-5-carboxylate (346 mg, 75%) as a yellow solid. This was used directly with no further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with MeOH
  3. filtrationThe resulting mixture was filtered
  4. customThe filtrate was purified by ion exchange chromatography
  5. washThe desired product was eluted from the column
  6. customwere evaporated to dryness

Sources & evidence

ORD record
ord-80b8d9ce25f441588d5433e82862296a
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Linked notes

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