tert-Butyl acrylate → HCID 58692462, compound

HRID 1362108Notes

Reaction equation

HRID 1362108 reaction equation
Br[C:2]1[CH:17]=[N:16][C:5]2[NH:6][C:7](=[O:15])[N:8]([CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])[CH2:9][C:4]=2[CH:3]=1.[C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])[CH:19]=[CH2:20].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]>[C:23]([O:22][C:18](=[O:21])/[CH:19]=[CH:20]/[C:2]1[CH:17]=[N:16][C:5]2[NH:6][C:7](=[O:15])[N:8]([CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])[CH2:9][C:4]=2[CH:3]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

8

Reactant 4

HCID 15458tert-Butyl acrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 59456910HCID 59456910, compound

Product 1

HCID 58692462HCID 58692462, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 7854PropionitrileSolvent

Procedure

To a solution of 6-bromo-3-(2-dimethylamino-ethyl)-3,4-dihydro-1H-pyrido[2,3-d]pyrimidin-2-one (240 mg, 0.802 mmol) in propionitrile (16 mL) and DMF (4 mL) was added tert-butyl acrylate (0.46 mL, 3.2 mmol) and (i-Pr)2EtN (0.28 mL, 1.6 mmol), Pd(OAc)2 (18 mg, 0.080 mmol) and P(o-tol)3 (49 mg, 0.16 mmol). The mixture was degassed with Ar for 15 min. The mixture was heated to reflux overnight, and then allowed to cool. The dark solution was filtered through a pad of Celite. The filtrate was concentrated. Purification by column chromatography (silica gel, CH2Cl2/MeOH/Et3N, 94/5.5/0.5) gave the title compound (150 mg, 54%) as a pale-yellow solid: MS (ESI) m/e 347 (M+H)+.

Workup

  1. customThe mixture was degassed with Ar for 15 min
  2. temperatureThe mixture was heated
  3. temperatureto reflux overnight
  4. temperatureto cool
  5. filtrationThe dark solution was filtered through a pad of Celite
  6. concentrationThe filtrate was concentrated
  7. customPurification by column chromatography (silica gel, CH2Cl2/MeOH/Et3N, 94/5.5/0.5)

Sources & evidence

ORD record
ord-a3ce30d8cd7049f0a166d91fdfdbdfae
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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