3-Chloro-4-pyridineboronic acid → 5-(3-Chloro-pyridin-4-yl)-N4-(tetrahydro-pyran-4-yl)-pyrimidine-2,4-diamine

HRID 79112

反応式

HRID 79112 の反応式
Br[C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1B(O)O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1

参加物

5

反応物 2

HCID 38618773-Chloro-4-pyridineboronic acidHCID 582996735-Bromo-N4-(tetrahydro-pyran-4-yl)-pyrimidine-2,4-diamine

生成物 1

HCID 583000215-(3-Chloro-pyridin-4-yl)-N4-(tetrahydro-pyran-4-yl)-pyrimidine-2,4-diamine収率 98%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
130 °C

実験手順

A mixture of compound 33 (2.03 g, 7.43 mmol), 3-chloropyridin-4-ylboronic acid (3.51 g, 22.3 mmol), and Pd(PPh3)2Cl2 (0.522 g, 0.743 mmol) in dioxane (44 ml) in a pressure vessel was purged with N2 for 20 minutes and to this mixture was added aq. Na2CO3 (1 M, 22 mL) by syringe. The reaction was further purged with N2 for another 20 minutes and then heated to 130° C. for 12 hours. DCM was added to the reaction and the mixture was washed with water and brine. The organic layer was dried with sodium sulfate and concentrated to provide compound 34 (2.07 g, crude, 98%) which was used in the next reaction without further purification. LCMS-ESI (POS), M/Z, M+1: Found 306.1, Calculated 306.1.

後処理

  1. customwas purged with N2 for 20 minutes and to this mixture
  2. additionwas added aq. Na2CO3 (1 M, 22 mL) by syringe
  3. customThe reaction was further purged with N2 for another 20 minutes
  4. additionDCM was added to the reaction
  5. washthe mixture was washed with water and brine
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-633972e782a343608819f24c9088577b
出典データセット
uspto-grants-2014_09
特許番号
US08841312B2

関連ノート

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