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1,4-Bis(diphenylphosphino)butane → Ethyl 6-amino-2-chloro-5-methoxypyrimidine-4-carboxylate

HRID 1988542
ノート
印刷プレビュー

反応式

HRID 1988542 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH3:10])=[C:4](Cl)[N:3]=1.[C:12]([O-:15])(=[O:14])C.[Na+].[CH:17]1C=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:18]=1>C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:17]([O:15][C:12]([C:4]1[C:5]([O:9][CH3:10])=[C:6]([NH2:8])[N:7]=[C:2]([Cl:1])[N:3]=1)=[O:14])[CH3:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 821241,4-Bis(diphenylphosphino)butaneHCID 517045Sodium AcetateHCID 591269272,6-Dichloro-5-methoxypyrimidin-4-amine

生成物 1

HCID 59126903Ethyl 6-amino-2-chloro-5-methoxypyrimidine-4-carboxylate収率 232.5%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒
HCID 702
Ethanol
溶媒

反応条件

温度
110 °C

実験手順

2,6-Dichloro-5-methoxypyrimidin-4-ylamine (5.0 g, 26 mmol) was combined in 75 mL absolute ethanol with sodium acetate (2.1 g, 26 mmol), palladium acetate (280 mg, 0.91 mmol) and DPPB (1.1 g, 2.6 mmol) in a 300 mL stirred pressure reactor. The reactor was purged and pressurized to 300 psi with carbon monoxide, and heated at 110° C. for 7 h. The volatiles were removed under vacuum and the residue was taken up in ethyl acetate and water. The aqueous phase was extracted with an additional ethyl acetate; and the combined extracts were washed with brine, dried and evaporated. The residue was purified by flash chromatography on silica gel (0-30% ethyl acetate gradient in hexanes) to give the title compound (1.4 g, 23% yield): mp 118-119° C. 1H NMR (CDCl3) δ 6.18 (br s, 2H), 4.45 (q, 2H), 3.91 (s, 3H), 1.42 (t, 3H).

後処理

  1. customThe reactor was purged
  2. customThe volatiles were removed under vacuum
  3. extractionThe aqueous phase was extracted with an additional ethyl acetate
  4. washand the combined extracts were washed with brine
  5. customdried
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica gel (0-30% ethyl acetate gradient in hexanes)

出典と根拠

ORDレコード
ord-7c12127ebb5249b681922313eb88b2d3
出典データセット
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07642220B2

反応ノート

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