Potassium Carbonate → 4-[(5-Cyano-2-methylsulfanyl-pyrimidin-4-ylamino)-methyl]-benzoic acid methyl ester

HRID 416263

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[CH3:12][O:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC>[CH3:12][O:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:1][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-amino-2-methylsulfanyl-pyrimidine-5-carbonitrile (229a) (200 mg, 1.2 mmol) in DME (10 ml) were added 4-bromomethyl-benzoic acid methyl ester (274 mg, 1.2 mmol) and K2CO3 (663 mg, 4.8 mmol) at room temperature. The reaction mixture was heated at 100° C. for 5 h, overnight at 60° C., cooled, filtered and concentrated in vacuo. The crude product was used in the next reaction without further purification. LRMS: 314.3 (calc.); 315.3 (obt.) (MH)+.

Workup

temperaturecooled
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was used in the next reaction without further purification

Sources & evidence

ORD record: ord-3cb4a625af9c4a8e86ccf1b2041c1224
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088805B2

Linked notes

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