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

HRID 2409099노트

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HRID 2409099 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

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

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온도
105 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-2f32becfc4ba46c2be66b15cd07c4a73
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815882B2

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