Trimethylsilylacetylene → HCID 59258895, compound

HRID 472219Notes

Reaction equation

C(N(C(C)C)CC)(C)C.[NH2:10][C:11]1[N:12]=[C:13]([CH3:27])[C:14]2[CH:20]=[C:19](Br)[C:18](=[O:22])[N:17]([CH:23]3[CH2:26][CH2:25][CH2:24]3)[C:15]=2[N:16]=1.[Si:28]([C:32]#[CH:33])([CH3:31])([CH3:30])[CH3:29]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.O1CCOCC1>[NH2:10][C:11]1[N:12]=[C:13]([CH3:27])[C:14]2[CH:20]=[C:19]([C:33]#[C:32][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:18](=[O:22])[N:17]([CH:23]3[CH2:26][CH2:25][CH2:24]3)[C:15]=2[N:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A flask was charged with Pd(PPh3)2Cl2 (84.2 mg, 0.120 mmol) and copper iodide (34.3 mg, 0.180 mmol). To this were added 1,4-dioxane (12 mL) and diisopropylethylamine (0.84 mL, 4.8 mmol) via syringe. 2-Amino-6-bromo-8-cyclobutyl-4-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (371 mg, 1.20 mmol) was introduced, and the resulting yellow solution was carefully sparged with nitrogen for 10 min. TMS-acetylene (0.50 mL, 3.6 mmol) was then added via syringe, and the resulting black solution was stirred at 70° C. for 1 h. Solvent was removed under reduced pressure. The crude solid was purified by flash chromatography on silica gel eluting with CHCl3 then 3% MeOH in CHCl3 to afford the title product (322 mg).

Workup

customthe resulting yellow solution was carefully sparged with nitrogen for 10 min
customSolvent was removed under reduced pressure
customThe crude solid was purified by flash chromatography on silica gel eluting with CHCl3

Sources & evidence

ORD record: ord-01b2bba4245a41a7960912920e7c30ab
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633204B2

Reaction notes

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