Sodium Sulfide → 4-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-pyrimidinamine

HRID 1159877Notes

Reaction equation

HRID 1159877 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[N:17]=[C:16]([C:18]4[C:19]([C:27]5[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-])=O)[CH:28]=5)=[N:20][N:21]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=45)[CH:15]=[CH:14][N:13]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[S-2].[Na+].[Na+]>C(O)C.O>[NH2:33][C:29]1[CH:28]=[C:27]([C:19]2[C:18]([C:16]3[CH:15]=[CH:14][N:13]=[C:12]([NH:11][C:9]4[CH:8]=[CH:7][C:6]5[O:1][CH2:2][CH2:3][O:4][C:5]=5[CH:10]=4)[N:17]=3)=[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][N:21]3[N:20]=2)[CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 14804Sodium SulfideHCID 59513715N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-[2-(3-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine

Product 1

HCID 595138174-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-pyrimidinamineYield 99.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-[2-(3-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine (1.09 g, 2.3 mmol) in ethanol (2 mL) was added sodium sulfide nonhydrate (2.76 g, 11.5 mmol) in H2O (2 mL). The mixture was heated at 80° C. for 16 h, allowed to cool to rt and filtered. The filtrate was concentrated to afford the product (1 g) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) 69.29 (s, 1H), 8.76 (d, 1H, J=7.2), 8.51 (d, 1H, J=8.8), 8.15 (d, 1H, J=5.2), 7.39-7.43 (m, 1H), 7.35 (m, 1H), 7.04-7.12 (m, 3H), 6.76-6.72 (m, 2H), 6.65-6.62 (m, 2H), 6.43 (d, 1H, J=5.2), 5.21 (s, 2H), 4.16-4.20 (m, 4H).

Workup

  1. temperatureto cool to rt
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-03fce357d1fa4138a6a2283f3e82c959
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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