Dimethylformamide → 2-Amino-4-chloro-6-cyano-pyrimidylacetate-t-butyl ester

HRID 230983

反応式

HRID 230983 の反応式
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])#N.[NH2:13][C:14]1[N:19]=[C:18]([Cl:20])[CH:17]=[C:16](Cl)[N:15]=1.C[N:23](C)C=O>>[C:9]([O:8][C:6](=[O:7])[CH2:5][C:3]1[C:18]([Cl:20])=[N:19][C:14]([NH2:13])=[N:15][C:16]=1[C:17]#[N:23])([CH3:12])([CH3:11])[CH3:10]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 655222-Amino-4,6-dichloropyrimidineHCID 70693tert-Butyl cyanoacetate

生成物 1

HCID 539121792-Amino-4-chloro-6-cyano-pyrimidylacetate-t-butyl ester

反応条件

温度
0 °C

実験手順

To a suspension of sodium hydride (17.6 g, 733 mmol) in dry N,N-dimethylformamide (DMF) at 0° C. was added dropwise t-butyl cyanoacetate (96 g, 680 mmol). The tan suspension was stirred at 0° C. for 0.5 hours then 2-amino-4,6-dichloropyrimidine (58.7 g, 358 mmol) was added batchwise. The mixture was heated slowly to 90° C. and the reaction was held at 90° C. for 18 hours. The reaction mixture was poured onto water (1 l) and the mixture was filtered. The filtrate was acidified with con HCl to pH 6 and the resultant solid was filtered and washed with water and hexanes and dried to furnish 99.64 g of the desired subject as a green powder, m.p. 107°-109° C. NMR (200 mHz) D6-acetone δ 12.8 (bs, 1 H), 8.0 (bs, 1 H), 7.8 (bs, 1 H), 6.3 (s, 1 H), 1.5 (s, 9 H).

後処理

  1. temperatureThe mixture was heated slowly to 90° C.
  2. waitthe reaction was held at 90° C. for 18 hours
  3. additionThe reaction mixture was poured onto water (1 l)
  4. filtrationthe mixture was filtered
  5. filtrationthe resultant solid was filtered
  6. washwashed with water and hexanes
  7. customdried
  8. customto furnish 99.64 g of the

出典と根拠

ORDレコード
ord-e99eef0083ba482a875cd85532f049a4
出典データセット
uspto-grants-1989_07
特許番号
US04844727

関連ノート

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