Ethanol → HCID 178477996, compound

HRID 639370Notes

Reaction equation

HRID 639370 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([Cl:16])[N:11]=2)=[CH:4][CH:3]=1.COC(OC)[N:21]([CH3:23])C.C(O)C.O.[NH2:30]N>>[Cl:16][C:12]1[N:11]=[C:10]([C:9]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:30][NH:21][CH:23]=2)[CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 11543539Ethanone, 1-(4-chlorophenyl)-2-(2-chloro-4-pyrimidinyl)-

Product 1

HCID 178477996HCID 178477996, compound

Conditions

Temperature
100 °C

Procedure

3.67 g (13.74 mMol) of 1-(4-Chloro-phenyl)-2-(2-chloro-pyrimidin-4-yl)-ethanone is suspended in 91.6 mL (50 Eq.) of N,N-dimethylformamid-dimethylacetal (Fluka puriss. 40271) and stirred for 2 h at 100° C. The dark brownish solution is freed from solvent under high vacuum at 30° C. The crude product, (Z)-1-(4-chloro-phenyl)-2-(2-chloro-pyrimidin-4-yl)-3-dimethylamino-propenone, is used for the next step without purification. To the solution of 5.42 g (14.2 mMol) of (Z)-1-(4-chloro-phenyl)-2-(2-chloro-pyrimidin-4-yl)-3-dimethylamino-propenone in 30 mL of ethanol 0.785 g (0.763 mL; 15.69 mMol, 1.1 Eq.) of hyrazine monohydrate (Fluka 53850) is added at rt. After stirring 45 min at rt, the yellow crystals are filtered off, washed with ethanol and dried at 60° C. under vacuum. The crude product is purified by recrystallization from methanol to obtain 2-chloro-4-[3-(4-chloro-phenyl)-1H-pyrazol-4-yl]-pyrimidine as slightly yellowish crystals.

Workup

  1. customis freed from solvent under high vacuum at 30° C
  2. customThe crude product, (Z)-1-(4-chloro-phenyl)-2-(2-chloro-pyrimidin-4-yl)-3-dimethylamino-propenone, is used for the next step without purification
  3. stirringAfter stirring 45 min at rt
  4. filtrationthe yellow crystals are filtered off
  5. washwashed with ethanol
  6. customdried at 60° C. under vacuum
  7. customThe crude product is purified by recrystallization from methanol

Sources & evidence

ORD record
ord-246c1137afdf478990c974124e5c597e
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

Loading…