Triethylamine → HCID 86630702, compound

HRID 1437429Notes

Reaction equation

HRID 1437429 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:19][C@H:20]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH2:21][OH:22]>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:19][C@H:20]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:21][OH:22])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 10583003(R)-2-Amino-2-(4-fluorophenyl)ethanol

Product 1

HCID 86630702HCID 86630702, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,4-dichloro-5-nitropyrimidine (1.5 g, 7.73 mmol) in EtOH (25 ml) at 0° C. was added triethylamine (1.6 ml, 11.6 mmol) and a solution of (2R)-2amino-2-(4-fluorophenyl)ethanol (prepared according to a procedure in J. Med. Chem. 1999, 42, 4981-5001, 1.2 g, 7.73 mmol). The reaction mixture was stirred at 0° C. for 3 hours. The solvent was removed and the residue was dissolved in EtOAc and was washed with water. The organic layer was concentrated. Flash chromatography on silica gel (20-50% EtOAc in hexanes) gave the title compound as a solid (703 mg, 29%). NMR (CDCl3) 4.00 (m, 2H), 5.50 (m, 1H), 7.07 (m, 2H), 7.38 (m, 2H), 9.04 (s, 1H), 9.10 (br s, 1H).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwas washed with water
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-6c3c8f2a9f9046c3b6603f9f5cc7ccb4
Source dataset
uspto-grants-2009_11
Patent number
US07622482B2

Reaction notes

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