Triethylamine → 4-(3-tert-Butoxycarbonylaminopropylamino)-2-chloropyrimidine-5-carboxylic acid

HRID 871860

Reaction equation

HRID 871860 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].C(OCC)(=O)C>C1COCC1>[C:26]([O:25][C:24]([NH:23][CH2:22][CH2:21][CH2:20][NH:19][C:6]1[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)=[O:30])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 219418962,4-Dichloro-5-pyrimidinecarboxylic acid

Product 1

HCID 866731374-(3-tert-Butoxycarbonylaminopropylamino)-2-chloropyrimidine-5-carboxylic acidYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.21 g (11.45 mmol) of 2,4-dichloro-5-pyrimidinecarboxylic acid prepared in step 2.3 (method B) in 20 mL of anhydrous THF is cooled to 2-5°C. on an ice bath. A solution of 4.79 mL (34.35 mmol) of triethylamine and 2 g (11.48 mmol) of tert-butyl (3-aminopropyl)carbamate in 15 mL of anhydrous THF is then added dropwise. The reaction mixture is stirred at room temperature for 30 minutes. Ethyl acetate is added and the organic phase is washed with aqueous 1N HCl and with water. The organic phases are combined, dried over sodium sulfate, filtered and concentrated under vacuum. 3.35 g of the expected product are obtained in the form of a yellow solid. Yield=88.6%.

Workup

  1. washthe organic phase is washed with aqueous 1N HCl and with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1a9afc175b754b5ea5efbc5e0b1ac308
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Linked notes

Loading…