tert-Butyl acrylate → HCID 59456936、化合物

HRID 1362103ノート

反応式

HRID 1362103 の反応式
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]

参加物

8

反応物 4

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

生成物 1

HCID 59456936HCID 59456936、化合物収率 83.5%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 7854Propionitrile溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-be25b85d9e06463991d4d14c1af1bd22
出典データセット
uspto-grants-2011_02
特許番号
US07879872B2

反応ノート

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