Diisopropylethylamine → HCID 66589803, compound

HRID 16901Notes

Reaction equation

HRID 16901 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][CH:13]([N:15]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[CH3:14].C(N(C(C)C)C(C)C)C>ClCCl>[CH3:12][CH:13]([N:15]1[CH2:21][CH2:20][CH2:19][N:18]([C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=2)[CH2:17][CH2:16]1)[CH3:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 122365131-Isopropyl-homopiperazineHCID 12627752Methyl 2-chloropyrimidine-5-carboxylate

Product 1

HCID 66589803HCID 66589803, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl 2-chloropyrimidine-5-carboxylate (209 mg, 1.21 mmol) in dichloromethane (4.00 ml) was added to a stirred solution of 1-propan-2-yl-1,4-diazepane (172 mg, 1.21 mmol) and N-ethyl-N-propan-2-ylpropan-2-amine (0.523 ml, 3.02 mmol) in dichloromethane (4.00 ml) at 25° C. The resulting solution was stirred at ambient temperature for 18 h. The reaction mixture was evaporated to dryness and redissolved in MeOH (20 mL) and the crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford methyl 2-(4-propan-2-yl-1,4-diazepan-1-yl)pyrimidine-5-carboxylate (267 mg, 79%) as a cream oil which crystallised on standing. This was used directly with no further purification.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in MeOH (20 mL)
  3. customthe crude product was purified by ion exchange chromatography
  4. washThe desired product was eluted from the column
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-034e917bbaf943f7aa112512ea8a04e5
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

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