Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate → 2-[(R)-4-(6-Chloro-4,5-dimethyl-pyridazin-3-yl)-2-methyl-piperazin-1-yl]-4-trifluoromethyl-pyrimidine-5-carboxylic acid ethyl ester

HRID 1479992Notes

Reaction equation

HRID 1479992 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:13]([F:16])([F:15])[F:14])=[N:8][C:9](Cl)=[N:10][CH:11]=1)=[O:5])[CH3:2].[Cl:17][C:18]1[N:19]=[N:20][C:21]([N:26]2[CH2:31][CH2:30][NH:29][C@H:28]([CH3:32])[CH2:27]2)=[C:22]([CH3:25])[C:23]=1[CH3:24]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:13]([F:16])([F:15])[F:14])=[N:8][C:9]([N:29]2[CH2:30][CH2:31][N:26]([C:21]3[N:20]=[N:19][C:18]([Cl:17])=[C:23]([CH3:24])[C:22]=3[CH3:25])[CH2:27][C@H:28]2[CH3:32])=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 2780355Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylateHCID 591915183-chloro-4,5-dimethyl-6-((R)-3-methyl-piperazin-1-yl)-pyridazine

Product 1

HCID 591914582-[(R)-4-(6-Chloro-4,5-dimethyl-pyridazin-3-yl)-2-methyl-piperazin-1-yl]-4-trifluoromethyl-pyrimidine-5-carboxylic acid ethyl esterYield 97.2%

Procedure

Following the protocol above with 2-chloro-4-trifluoromethyl-pyrimidine-5-carboxylic acid ethyl ester (400 mg, 1.57 mmol, 1 eq) and 3-chloro-4,5-dimethyl-6-((R)-3-methyl-piperazin-1-yl)-pyridazine (400 mg, 1.66 mmol, 1 eq) affords 700 mg of desired product as a white solid (97%).

Sources & evidence

ORD record
ord-3308ada6e9b24e7fa1ab3662d359a8f2
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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