Water → 6-(4-Chlorobenzoyl)-3-propargyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-dione

HRID 1500610Notes

Reaction equation

HRID 1500610 reaction equation
Cl.[CH2:2]([N:5]1[C:10](=[O:11])[C:9]2[CH2:12][NH:13][CH2:14][CH2:15][C:8]=2[NH:7][C:6]1=[O:16])[C:3]#[CH:4].C(N(CC)CC)C.[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1.O>C(Cl)Cl>[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([N:13]2[CH2:14][CH2:15][C:8]3[NH:7][C:6](=[O:16])[N:5]([CH2:2][C:3]#[CH:4])[C:10](=[O:11])[C:9]=3[CH2:12]2)=[O:30])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 866631133-Propargyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-dione hydrochloride

Product 1

HCID 866631156-(4-Chlorobenzoyl)-3-propargyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-propargyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-dione hydrochloride (790 mg) was suspended in methylene chloride, triethylamine (0.95 ml) and 4-chlorobenzoyl chloride (0.42 ml) were added under ice cooling and the resultant mixture was stirred at the same temperature for 30 minutes. To the reaction solution, water was added and the resultant mixture was concentrated. To the residue, diethyl ether was added and insoluble matter was separated by filtration to obtain the titled compound (894 mg) as a white powder. The resultant compound was used in a next reaction without further purifying.

Workup

  1. concentrationthe resultant mixture was concentrated
  2. additionTo the residue, diethyl ether was added
  3. custominsoluble matter was separated by filtration

Sources & evidence

ORD record
ord-8e705ba5bc344863b0bd715a0f1ae6f4
Source dataset
uspto-grants-2015_12
Patent number
US09206173B2

Reaction notes

Loading…