6-chloro-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile → HCID 20237897, compound

HRID 365193Notes

Reaction equation

HRID 365193 reaction equation
[Cl:1][C:2]1[N:3]([CH3:13])[C:4](=[O:12])[N:5]([CH3:11])[C:6](=[O:10])[C:7]=1[C:8]#[N:9].[O:14]([CH2:21][CH:22]([OH:28])[CH2:23][NH:24][CH2:25][CH2:26][NH2:27])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[ClH:1].[O:14]([CH2:21][CH:22]([OH:28])[CH2:23][NH:24][CH2:25][CH2:26][NH:27][C:2]1[N:3]([CH3:13])[C:4](=[O:12])[N:5]([CH3:11])[C:6](=[O:10])[C:7]=1[C:8]#[N:9])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 122056876-chloro-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrileHCID 145507661-[(2-Aminoethyl)amino]-3-phenoxypropan-2-ol

Product 1

HCID 20237897HCID 20237897, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g. 4-Chloro-5-cyano-1,3-dimethylpyrimidine-2,6(1H,3H)-dione are added in small portions, with cooling, to a solution of 5.26 g. 1-phenoxy-3-(2-aminoethylamino)-propan-2-ol in 20 ml. dimethylformamide. The reaction mixture is stirred for 2 hours at ambient temperature, mixed with 60 ml. isopropyl alcohol, filtered with suction and the solid obtained subsequently washed with isopropyl alcohol. There are obtained 8.7 g. (85% of theory) of the desired product in the form of colorless crystals; m.p. 202°-204° C.

Workup

  1. temperaturewith cooling, to a solution of 5.26 g
  2. additionmixed with 60 ml
  3. filtrationisopropyl alcohol, filtered with suction
  4. customthe solid obtained subsequently
  5. washwashed with isopropyl alcohol
  6. customThere are obtained 8.7 g

Sources & evidence

ORD record
ord-1551cdca9a754b47b3087df2e60c6db9
Source dataset
uspto-grants-1986_08
Patent number
US04608383

Reaction notes

Loading…