tert-Butyl acrylate → HCID 59456972, compound

HRID 1711849Notes

Reaction equation

HRID 1711849 reaction equation
Br[C:2]1[CH:13]=[N:12][C:5]2[NH:6][C:7](=[O:11])[NH:8][C:9](=[O:10])[C:4]=2[CH:3]=1.[C:14]([O:18]C(C)(C)C)(=[O:17])[CH:15]=[CH2:16].C(N(C(C)C)C(C)C)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)CC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:11]=[C:7]1[NH:6][C:5]2[N:12]=[CH:13][C:2](/[CH:16]=[CH:15]/[C:14]([OH:18])=[O:17])=[CH:3][C:4]=2[C:9](=[O:10])[NH:8]1

Participants

8

Reactant 4

HCID 15458tert-Butyl acrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 235841046-Bromopyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 59456972HCID 59456972, compoundYield 103.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 7854PropionitrileSolvent

Procedure

A suspension of 6-bromo-1H-pyrido[2,3-d]pyrimidine-2,4-dione (430 mg, 1.59 mmol) in propionitrile (8 mL) and DMF (2 mL) was treated with tert-butyl acrylate (0.93 mL, 6.4 mmol), (i-Pr)2EtN (0.6 mL, 3.3 mmol) and P(o-tol)3 (100 mg, 0.32 mmol). The solution was deoxygenated with Ar for 20 min. Pd(OAc)2 (36 mg, 0.16 mmol) was added and the mixture was deoxygenated with a stream of Ar for 10 min. The mixture was heated to reflux for 17 h, then allowed to cool. The resulting precipitate was isolated by filtration to give the title compound (384 mg, 83%) as a gray solid: 1H NMR (300 MHz, DMSO-d6) δ 11.88 (s, 1H), 11.54 (s, 1H), 8.96 (d, J=2.2 Hz, 1H), 8.53 (d, J=2.2 Hz, 1H), 7.65 (d, J=16.1 Hz, 1H), 6.72 (d, J=16.1 Hz, 1H), 1.49 (s, 9H); ESI MS m/e 290 (M+H)+.

Workup

  1. customThe solution was deoxygenated with Ar for 20 min
  2. customthe mixture was deoxygenated with a stream of Ar for 10 min
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 17 h
  5. temperatureto cool
  6. customThe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-ed9e2f64966941678584a4e3cb246b14
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

Loading…