Potassium Carbonate → HCID 18507388, compound

HRID 1356090Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6](Br)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH3:13])[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 250 mg (1.02 mmol) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile in 10 ml toluene at room temperature were added 310 mg (2.04 mmol) 2-methoxybenzeneboronic acid, 118 mg (0.10 mmol) tetrakis(triphenylphosphine) palladium(O) and 262 mg (2.04 mmol) potassium carbonate. The reaction mixture was heated at 100° C. for 16 h, then cooled to room temperature and partitioned between ethyl acetate and water. The phases were separated and the organic phase dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate/hexane 1/4 then ethyl acetate/hexane 1/2) followed by trituration in hexane afforded 80 mg (29%) 2-amino-4-(2-methoxy-phenyl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a white crystalline solid. EI-MS m/e (%): 272 (M+, 32), 257 ([M—CH3]+, 100), 241 (17).

Workup

temperaturecooled to room temperature
custompartitioned between ethyl acetate and water
customThe phases were separated
dry with materialthe organic phase dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9aa143490543469e9b792c93523558c1
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

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