4-Bromophenacyl bromide → 4-((3-Chloro-4-fluorophenyl)amino)-7-methyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one

HRID 1072158노트

반응식

HRID 1072158 반응식
C1C(C(CBr)=[O:8])=CC=C(Br)C=1.[Cl:12][C:13]1[CH:14]=[C:15]([NH:20][C:21]2[C:22]3[CH:29]=[CH:28][N:27]([CH3:30])[C:23]=3[N:24]=[CH:25][N:26]=2)[CH:16]=[CH:17][C:18]=1[F:19]>C(O)(C)(C)C.C(O)(=O)C.[Zn]>[Cl:12][C:13]1[CH:14]=[C:15]([NH:20][C:21]2[C:22]3[CH2:29][C:28](=[O:8])[N:27]([CH3:30])[C:23]=3[N:24]=[CH:25][N:26]=2)[CH:16]=[CH:17][C:18]=1[F:19]

참가 물질

6

반응물 2

HCID 74544-Bromophenacyl bromideHCID 22390983N-(3-Chloro-4-fluorophenyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

생성물 1

HCID 223909724-((3-Chloro-4-fluorophenyl)amino)-7-methyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one수율 98.1%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 6386tert-Butanol용매

실험 절차

PBPB (2.8 g, 7.8 mmol) was added portionwise to the (3-chloro-4-fluoro-phenyl)-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine (1.08 g, 3.9 mmol) suspended in tert-butanol (20 mL) and acetic acid (10 mL). After stirring at room temperature for 18 hours, to the mixture was added zinc dust (760 mg, 11.7 mmol) portionwise and stirring was continued for overnight. The precipitate was filtered off and the filtrate was concentrated. The residue was triturated with little water and the precipitate was collected by vacuum filtration, washed with little ethyl acetate and dried to give 1.12 g (98%) of 4-(3-chloro-4-fluoro-phenylamino)-7-methyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one as a tan colored solid. 1H NMR (DMSO-d6) 9.07 (s, 1H, NH), 8.42 (s, 1H), 8.01 (d, J=2.6 & 7.2 Hz, 1H), 7.56 (m, 1H), 7.34 (t, J=9.1 Hz, 1H), 3.48 (s, 2H, CH2), 3.07 (s, 3H, CH3).

후처리

  1. stirringstirring
  2. waitwas continued for overnight
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was triturated with little water
  6. filtrationthe precipitate was collected by vacuum filtration
  7. washwashed with little ethyl acetate
  8. customdried

출처 및 근거

ORD 기록
ord-5fdfd01617bd4aa49fcf11a41bb1d36f
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908930B2

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