Potassium Hydroxide → 8-ethyl-6-(1H-imidazol-5-yl)-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-imine

HRID 1893909Notes

Reaction equation

[OH-].[K+].[CH2:3]([NH:5][C:6]1[C:11]([CH:12]=O)=[C:10]([CH3:14])[N:9]=[C:8]([S:15][CH3:16])[N:7]=1)[CH3:4].C(N1[C:24]2[N:25]=[C:26]([NH:30][CH2:31]C)[N:27]=[C:28](C)[C:23]=2C=C(C2N(C(OC(C)(C)C)=O)C=CC=2)C1=O)C.N1C(CC#N)=CN=C1>C(O)C>[CH2:3]([N:5]1[C:6]2[N:7]=[C:8]([S:15][CH3:16])[N:9]=[C:10]([CH3:14])[C:11]=2[CH:12]=[C:23]([C:24]2[NH:25][CH:26]=[N:30][CH:31]=2)[C:28]1=[NH:27])[CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of potassium hydroxide (0.139 g, 2.48 mmol) in absolute ethanol (3.0 mL) was added to a pressure tube charged with 4-(ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carbaldehyde (0.229 g, 1.08 mmol), prepared using procedures similar to those described for Intermediate 1, and 2-(1H-imidazol-5-yl)acetonitrile (0.174 g, 162 mmol) and heated to 70° C. After 12 h, the reaction was allowed to cool to room temperature and concentrated in vacuo affording 8-ethyl-6-(1H-imidazol-5-yl)-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-imine as a solid. The product was used in the subsequent step without further purification.

Workup

customprepared
temperatureto cool to room temperature
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b1dda0cf24bd402f9b4effb8acb2d3a8
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513266B2

Reaction notes

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