Ammonia → 6-aminocarbonyl-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

HRID 567759노트

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HRID 567759 반응식
[C:1]([C:4]1[NH:20][C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:6]=2[CH:5]=1)(O)=[O:2].C[N:22]1CCOCC1.ClC(OCC(C)C)=O.N>C1COCC1.CN1C(=O)N(C)CCC1.O1CCOCC1>[NH2:22][C:1]([C:4]1[NH:20][C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:6]=2[CH:5]=1)=[O:2]

참가 물질

8

반응물 4

HCID 222AmmoniaHCID 79724-Methylmorpholine2회HCID 62365Isobutyl chloroformate2회HCID 212626746-carboxy-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

생성물 1

HCID 212626756-aminocarbonyl-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 312751,4-Dioxane용매HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-용매

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온도
0 °C

실험 절차

Alternative stage 10.1: A mixture of 2.165 g (7.5 mmol) of 6-carboxy-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine in 60 ml of THF and 10 ml of DMPU is heated under reflux for 30 min and then cooled to 0° C., whereupon a fine suspension is obtained. 824 μl (7.5 mmol) of N-methylmorpholine followed by 981 μl (7.5 mmol of isobutyl chloroformate in 10 ml of THF and, after 1 h at 0° C., 824 μl (7.5 mmol) of N-methylmorpholine followed by 981 μl (7.5 mmol) of isobutyl chloroformate again are added dropwise. The mixture is stirred for 1 h and then added dropwise to 70 ml of a saturated solution of ammonia in dioxane. After 3 h, the mixture is concentrated in vacuo. The residue is poured into water, and the precipitate is filtered off and washed with water and boiling isopropanol, whereupon 6-aminocarbonyl-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine is obtained. Further product is obtained from the isopropanol filtrate.

후처리

  1. temperatureis heated
  2. temperatureunder reflux for 30 min
  3. customis obtained
  4. additionagain are added dropwise
  5. waitAfter 3 h
  6. concentrationthe mixture is concentrated in vacuo
  7. additionThe residue is poured into water
  8. filtrationthe precipitate is filtered off
  9. washwashed with water

출처 및 근거

ORD 기록
ord-881df644cf3a42fc92752395e77e9f7b
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180636B2

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