Water → HCID 69057717, compound

HRID 1727236Notes

Reaction equation

HRID 1727236 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][NH:5][C:4](Cl)(C)[N:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[CH2:18](N(CC)CC)C.O>CN(C)C(=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:18])[N:5]=[C:4]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 8471TriethylamineHCID 136400722HCID 136400722, compound

Product 1

HCID 69057717HCID 69057717, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 4-amino-2-chloro-2-methylpyrimidine-5-carbonitrile (Maybridge, 100 mg, 0.6 mmol), piperazine (207 mg, 2.4 mmol), and triethylamine (71 mg, 0.7 mmol) in N,N-dimethylacetamide (20 ml) was heated to 108° C. for 6 h. The reaction mixture was stirred at ambient temperature for 18 h before pouring into water (400 ml) and extracting with ethyl acetate (3×30 ml), and then dichloromethane (20 ml). The combined organic extracts were washed with water (3×150 ml), and then dried (MgSO4) and concentrated to give a yellow solid (120 mg). The crude solid was pre-absorbed onto silica gel (250 mg) and then purified by flash chromatography on silica gel (20 g) eluting with ethyl acetate:methanol (90:10 and then 80:20) to give the title compound as a white solid (28 mg).

Workup

  1. extractionextracting with ethyl acetate (3×30 ml)
  2. washThe combined organic extracts were washed with water (3×150 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c9a7bb872c0f445dbca874b4ddf84c9d
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

Loading…