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Cesium carbonate → 7-(3-Methylpyridin-2-yl)-N-(5-(trifluoromethyl)pyrimidin-2-yl)-[1,8]naphthyridin-4-amine

HRID 1724877
ノート
印刷プレビュー

反応式

HRID 1724877 の反応式
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=1)=[N:7]2.[NH2:19][C:20]1[N:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:18][C:17]1[C:12]([C:6]2[N:7]=[C:8]3[C:3]([C:2]([NH:19][C:20]4[N:21]=[CH:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][N:25]=4)=[CH:11][CH:10]=[N:9]3)=[CH:4][CH:5]=2)=[N:13][CH:14]=[CH:15][CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 152735745-(Trifluoromethyl)pyrimidin-2-amineHCID 575610685-Chloro-2-(3-methylpyridin-2-yl)-1,8-naphthyridine

生成物 1

HCID 575610537-(3-Methylpyridin-2-yl)-N-(5-(trifluoromethyl)pyrimidin-2-yl)-[1,8]naphthyridin-4-amine

試薬・触媒・溶媒

2
HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

Heat a mixture of 5-chloro-2-(3-methylpyridin-2-yl)-[1,8]naphthyridine (51 mg, 0.2 mmol), 2-amino-5-trifluoromethylpyrimidine (42.0 mg, 0.25 mmol), xantphos (11.6 mg, 0.02 mmol), Pd2(dba)3 (18.3 mg, 0.02 mmol) and Cs2CO3 (130 mg, 0.4 mmol) in dioxane (2.0 mL) at 100° C. for 20 hours. Cool the mixture, concentrate under vacuum, dilute with EtOAc/water (5.0 mL each), filter through celite, wash celite with EtOAc (2×5 mL) and dry the combined organic layers with MgSO4. Filter the dried extract and concentrate under vacuum to afford the crude product. Purify by column chromatography using EtOAc as eluent to afford the title compound as a yellow solid. 1H NMR (400 MHZ, DMSO-D6) δ 10.92 (s, 1H), 9.0 (m, 3H), 8.92 (d, 1H, J=1.8 Hz), 8.58 (d, 1H, J=1.0 Hz), 8.12 (m, 2H), 7.80(d, 1H, J=2.1 Hz), 7.41 (dd, 1H), 2.65 (s, 3H). MS=383.3 (M+H).

後処理

  1. temperatureHeat
  2. temperatureCool the mixture
  3. concentrationconcentrate under vacuum
  4. additiondilute with EtOAc/water (5.0 mL each)
  5. filtrationfilter through celite
  6. washwash celite with EtOAc (2×5 mL)
  7. dry with materialdry the combined organic layers with MgSO4
  8. filtrationFilter the dried
  9. extractionextract
  10. concentrationconcentrate under vacuum
  11. customto afford the crude product
  12. customPurify by column chromatography

出典と根拠

ORDレコード
ord-e47c6db8b76e4a7fb3dee26fb1fe4610
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07488740B2

反応ノート

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