Sodium Carbonate → 4-chloro-7-methyl-5-(naphthalen-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 238029

反応式

HRID 238029 の反応式
[Cl:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([CH3:12])[C:4]=2[N:5]=[CH:6][N:7]=1.B(O)(O)[C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[C:3]2[C:10]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=3)=[CH:9][N:8]([CH3:12])[C:4]=2[N:5]=[CH:6][N:7]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 426094624-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 249052694-chloro-7-methyl-5-(naphthalen-2-yl)-7H-pyrrolo[2,3-d]pyrimidine収率 26.2%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (19 mg, 0.065 mmol), naphthalen-2-yl-2-boronic acid (12.2 mg, 0.071 mmol), Na2CO3 (68.9 mg, 0.65 mmol) and PdCl2(dppf) (26.5 mg, 0.00325 mmol) in THF (3 mL) was heated to reflux overnight under an argon atmosphere. Reaction was concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield ZK102 (5 mg, 26% yield). ESI-MS (M+H)+ m/z calcd 294.1, found 294.3.

後処理

  1. temperatureto reflux overnight under an argon atmosphere
  2. customReaction
  3. concentrationwas concentrated in vacuo
  4. custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)

出典と根拠

ORDレコード
ord-dfaa7f9fb08240b5acc19bdf0a98b165
出典データセット
uspto-grants-2014_02
特許番号
US08642604B2

関連ノート

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