Dimethylformamide → 2-(1,5-dimethyl-1H-pyrazol-4-ylamino)-4-(methylamino)pyrimidine-5-carbonitrile

HRID 2409099

反応式

HRID 2409099 の反応式
Br[C:2]1[C:3]([NH:16][CH3:17])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:15])[C:13]=2[CH3:14])=[N:6][CH:7]=1.[CH3:18][N:19](C=O)C>[C-]#N.[Zn+2].[C-]#N.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].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.[Fe+2]>[CH3:15][N:12]1[C:13]([CH3:14])=[C:9]([NH:8][C:5]2[N:4]=[C:3]([NH:16][CH3:17])[C:2]([C:18]#[N:19])=[CH:7][N:6]=2)[CH:10]=[N:11]1

参加物

6

反応物 2

HCID 6228DimethylformamideHCID 690819335-bromo-N2-(1,5-dimethyl-1H-pyrazol-4-yl)-N4-methylpyrimidine-2,4-diamine

生成物 1

HCID 690931072-(1,5-dimethyl-1H-pyrazol-4-ylamino)-4-(methylamino)pyrimidine-5-carbonitrile収率 25%

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
105 °C

実験手順

To a mixture of 5-bromo-N2-(1,5-dimethyl-1H-pyrazol-4-yl)-N4-methylpyrimidine-2,4-diamine (95 mg, 0.32 mmol), zinc cyanide (70 mg, 0.60 mmol), Pd2(dba)3 (11 mg, 0.012 mmol), DPPF (13 mg, 0.023 mmol) was added DMF (3.5 mL). The reaction was then heated in a sealed tube at 105° C. for 18 h. The reaction mixture was filtered and concentrated. The crude product was purified by reverse phase HPLC to give 2-(1,5-dimethyl-1H-pyrazol-4-ylamino)-4-(methylamino)pyrimidine-5-carbonitrile (19 mg, 25%). LCMS (Method A): [MH+]=244.1 at 2.53 min. 1H-NMR (DMSO): δ 8.96 (m, 1H), 8.21 (m, 1H), 7.49 (m, 2H), 3.69 (s, 3H), 2.84 (m, 3H), 2.14 (m, 3H). K1=0.025.

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe crude product was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-2f32becfc4ba46c2be66b15cd07c4a73
出典データセット
uspto-grants-2014_08
特許番号
US08815882B2

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