tert-Butyl acrylate → HCID 59456936, 화합물

HRID 1362103노트

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HRID 1362103 반응식
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:19]([CH3:22])([CH3:21])[CH3:20])(=[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]>[C:19]([O:18][C:14](=[O:17])/[CH:15]=[CH:16]/[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)([CH3:22])([CH3:21])[CH3:20]

참가 물질

8

반응물 4

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

생성물 1

HCID 59456936HCID 59456936, 화합물수율 83.5%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 7854Propionitrile용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-be25b85d9e06463991d4d14c1af1bd22
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879872B2

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