4-Amino-6-chloropyrimidine → HCID 86686852、化合物

HRID 402955ノート

反応式

HRID 402955 の反応式
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[Cl:16][C:17]1[N:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=1.CN(C1C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=CC=1)C.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:16][C:17]1[N:22]=[CH:21][N:20]=[C:19]([NH:23][C:2]2[N:7]=[CH:6][C:5]([C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[O:9])=[CH:4][CH:3]=2)[CH:18]=1

参加物

7

反応物 4

HCID 2380124-Amino-6-chloropyrimidineHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 65809001(6-Bromopyridin-3-YL)(morpholino)methanone

生成物 1

HCID 86686852HCID 86686852、化合物収率 40%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
150 °C

実験手順

To a stirred solution of (6-bromopyridin-3-yl)(morpholino)methanone (0.75 g, 2.78 mmol) in toluene (5 mL) was added 6-chloropyrimidin-4-amine (0.43 g, 3.33 mmol), Pd2(dba)3 (100 mg, 0.3 mmol), Davephos (157 mg, 0.4 mmol) and NaOt-Bu (848 mg, 8 mmol). The mixture was stirred at 150° C. for 13 hrs under N2. The mixture was evaporated and the residue was taken up in ethyl acetate (50 mL) and H2O (20 mL). The organic phase was washed with H2O (2×20 mL) and then brine (2×20 mL) and dried over Na2SO4. After filtration and concentration, the final product (350 mg, 40%) was obtained as yellow solid. LC-MS: 320.1 [M+H]+, tR=1.306 min.

後処理

  1. customThe mixture was evaporated
  2. washThe organic phase was washed with H2O (2×20 mL)
  3. dry with materialbrine (2×20 mL) and dried over Na2SO4
  4. filtrationAfter filtration and concentration

出典と根拠

ORDレコード
ord-8ecc71e327bd49ab9e1f105ee9f6ffa4
出典データセット
uspto-grants-2014_06
特許番号
US08742098B2

反応ノート

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