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

HRID 397402ノート

反応式

HRID 397402 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒HCID 6386tert-Butanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1a7d2d88001846aab57602f4519d8e48
出典データセット
uspto-grants-2003_08
特許番号
US06610688B2

反応ノート

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