Triethylamine → HCID 178497705, compound

HRID 1108266Notes

Reaction equation

HRID 1108266 reaction equation
[CH:1]([C:3]1[NH:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1)=[CH2:2].[C:12]([NH:18][C:19]1[N:20]=[C:21]([OH:30])[C:22]2[CH:28]=[C:27](Br)[CH:26]=[N:25][C:23]=2[N:24]=1)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:12]([NH:18][C:19]1[N:20]=[C:21]([OH:30])[C:22]2[CH:28]=[C:27]([CH:2]=[CH:1][C:3]3[NH:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=3)[CH:26]=[N:25][C:23]=2[N:24]=1)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 18784657Methyl 5-ethenyl-1H-pyrrole-2-carboxylateHCID 178447249HCID 178447249, compound

Product 1

HCID 178497705HCID 178497705, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 5-vinylpyrrole-2-carboxylate (298 mg, 2.0 mmol), 2-pivaloylamino4-hydroxy-6-bromopyrido[2,3-d]pyrimidine (683 mg, 2.1 mmol), palladium acetate (22.5 mg, 0.1 mmol), tri-o-tolylphosphine (60.9 mg, 0.2 mmol), and triethylamine (7.0 mL) in acetonitrile (20 mL) was heated overnight at reflux. The reaction mixture was cooled to room temperature, and the solid which formed collected by filtration, washed with cold acetonitrile, and dried to give methyl 5-[2-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)ethenyl]pyrrole-2-carboxylate as a yellow solid (706 mg, 89%). The product can be used in the next step without further purification. An analytical sample, mp >260° C., was obtained by recrystallization from methanol: 1H NMR (DMSO-d6) δ 12.28 (s, 1H), 12.08 (s, 1H), 11.40 (s, 1H), 8.93 (s, 1H), 8.40 (s, 1H), 7.36 (d, 1H, J=16.6 Hz), 7.27 (d, 1H, J=16.6 Hz), 6.81 (m, 1H), 6.48 (m, 1H), 3.76 (s, 3H), 1.23 (s, 9H).

Workup

  1. temperaturewas heated overnight
  2. temperatureat reflux
  3. customthe solid which formed
  4. filtrationcollected by filtration
  5. washwashed with cold acetonitrile
  6. customdried

Sources & evidence

ORD record
ord-a4e8af4d9e754a7b9565f9314ec2e94d
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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