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

HRID 230983

반응식

HRID 230983 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e99eef0083ba482a875cd85532f049a4
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04844727

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