Cesium carbonate → 2-[[(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methyl](methyl)amino]-5-[(1-methyl-1H-pyrazol-4-yl)methyl]-4(1H)-pyrimidinone trifluoroacetate

HRID 706028Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH3:20])[C:17]([NH2:19])=[NH:18])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].[C:25]([O-:28])([O-])=[O:26].[Cs+].[Cs+].[OH:31]/[CH:32]=[C:33](/[CH2:38][C:39]1[CH:40]=[N:41][N:42]([CH3:44])[CH:43]=1)\[C:34](OC)=O>CN1C(=O)CCC1>[F:22][C:21]([F:24])([F:23])[C:25]([OH:28])=[O:26].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH3:20])[C:17]3[NH:19][CH:34]=[C:33]([CH2:38][C:39]4[CH:40]=[N:41][N:42]([CH3:44])[CH:43]=4)[C:32](=[O:31])[N:18]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:21]([F:22])([F:23])[F:24]

Participants

Conditions

Temperature: 130 °C

Procedure

To the mixture of N-[(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methyl]-N-methylguanidine (50 mg, 0.140 mmol) and Cs2CO3 (182 mg, 0.559 mmol) in NMP (1 mL), was added methyl (2Z)-3-hydroxy-2-[(1-methyl-1H-pyrazol-4-yl)methyl]-2-propenoate (40 mg, 0.204 mmol). It was heated with a microwave reactor at 130° C. for 1 h. Purification via MDAP then afforded the title compound as a white solid (13 mg, 15.1% yield). LCMS: rt=3.03 min, [M+H+]=504

Workup

customPurification via MDAP

Sources & evidence

ORD record: ord-3fe3c667ba9e4643a57874ce38ba1aee
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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