Triethylamine → HCID 178497680, compound

HRID 1108262Notes

Reaction equation

HRID 1108262 reaction equation
I[C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:3]=1.[C:21]([NH:27][C:28]1[N:29]=[C:30]([OH:40])[C:31]2[CH:37]=[C:36]([C:38]#[CH:39])[CH:35]=[N:34][C:32]=2[N:33]=1)(=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C>C(#N)C>[C:21]([NH:27][C:28]1[N:29]=[C:30]([OH:40])[C:31]2[CH:37]=[C:36]([C:38]#[C:39][C:2]3[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:3]=3)[CH:35]=[N:34][C:32]=2[N:33]=1)(=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 187846613-Iodo-5-methoxycarbonyl-1-triisopropylsilylpyrroleHCID 178437079HCID 178437079, compound

Product 1

HCID 178497680HCID 178497680, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-iodo-5-methoxycarbonyl-1-triisopropylsilylpyrrole (1.222 g, 3.0 mmol), 2-pivaloylamino-4-hydroxy-6-ethynylpyrido[2,3-d]pyrimidine (0.851 g, 3.15 mmol), Pd(PPh)2C12 (105 mg, 0.15 mmol), cuprous iodide (2 g mg, 0.15 mmol), and triethylamine (0.5 mL) in acetonitrile (50 mL) was heated at reflux for 4 hours. The resulting solution was cooled, filtered, and concentrated in vacuo. The residue was purified by flash chromatography, eluting with hexanes:ethyl acetate(2:1). The first major fraction is unchanged starting material (270 mg, 32%); the subsequent major fluorescent fractions were combined and concentrated in vacuo to give methyl 4-[2-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)ethynyl]1-triisopropylsilylpyrrole-2-carboxylate as a pale yellow solid (935 mg, 57%, mp 163-165° C.): 1H NMR (CDCl3) δ 8.90 (br s, 1H), 8.52 (d, 1H, J=2.4 Hz), 7.35 (d, 1H, J=1.4 Hz), 7.23 (d, 1H, J=1.4 Hz), 3.79 (s, 3H), 1.75 (sept, 3H, J=7.6 Hz), 1.31 (s, 9H), 1.10(d, 18H, J=7.6 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe resulting solution was cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting with hexanes:ethyl acetate(2:1)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b02adbfded643069a96a747550ce979
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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