Water → HCID 178517832, compound

HRID 574121Notes

Reaction equation

HRID 574121 reaction equation
Cl[CH2:2][C:3]1[NH:12][C:11](=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[N:14]1([C:20]2[N:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)CC)C.O>CN(C=O)C>[N:21]1[CH:22]=[CH:23][CH:24]=[N:25][C:20]=1[N:14]1[CH2:19][CH2:18][N:17]([CH2:2][C:3]2[NH:4][C:5]3[C:10]([C:11](=[O:13])[N:12]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 887471-(2-Pyrimidinyl)piperazineHCID 1354173742-(chloromethyl)quinazolin-4(3H)-one

Product 1

HCID 178517832HCID 178517832, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

300 mg of 2-(chloromethyl)quinazolin-4(3H)-one and 300 mg 2-(piperazin-1-yl)pyrimidine were dissolved in 5 ml of DMF at room temperature. After a few seconds, 0.5 ml of triethylamine was added, and the reaction mixture was stirred at ambient temperature, while being monitored by TLC. Once the reaction was completed (overnight), additional 0.2 ml of triethylamine was added, followed by 3 ml of water, and the mixture was cooled to 0° C. The solid precipitate was thereafter collected by vacuum filtration, washed with cold water and dried for 2 hours at 50° C., to give 370 mg (75% yield) of the product.

Workup

  1. waitAfter a few seconds
  2. additionwas added
  3. temperaturethe mixture was cooled to 0° C
  4. filtrationThe solid precipitate was thereafter collected by vacuum filtration
  5. washwashed with cold water
  6. customdried for 2 hours at 50° C.

Sources & evidence

ORD record
ord-739a84cbdd9e41b4a92f477c7d6fe241
Source dataset
uspto-grants-2015_05
Patent number
US09034872B2

Reaction notes

Loading…