2-(Pyridin-4-yl)malonaldehyde → 3-Pyridin-2-yl-6-pyridin-4-yl-pyrazolo[1,5-a]pyrimidin-2-ylamine

HRID 490110Notes

Reaction equation

HRID 490110 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([NH2:13])=[N:9][NH:10][C:11]=1[NH2:12].[N:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH:23]=O)[CH:21]=O)=[CH:16][CH:15]=1>C(O)C.C(O)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:11]([NH2:12])=[N:10][N:9]2[CH:23]=[C:20]([C:17]3[CH:18]=[CH:19][N:14]=[CH:15][CH:16]=3)[CH:21]=[N:13][C:8]=12

Participants

5

Reactant 2

HCID 27372462-(Pyridin-4-yl)malonaldehydeHCID 576745884-(Pyridin-2-yl)-1H-pyrazole-3,5-diamine

Product 1

HCID 116521913-Pyridin-2-yl-6-pyridin-4-yl-pyrazolo[1,5-a]pyrimidin-2-ylamineYield 62%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-pyridin-2-yl-1H-pyrazole-3,5-diamine (290 mg, 1.66 mmol) and 2-pyridin-4-yl-malonaldehyde (247 mg, 1.66 mmol) were placed in ethanol (5 mL) with a catalytic amount of acetic acid (6 drops). The reaction mixture was submitted to microwave irradiations at 140° C. for 15 minutes. The crude mixture was cooled down to room temperature and the resulting precipitate was filtered and washed with more ethanol to provide the title as a golden yellow solid (295 mg, 62%). MS (ES+) 289, (ES−) 287. δH (DMSO-d6) 7.16 (1H, dd), 7.21 (2H, m), 7.84 (1H, m), 7.89 (2H, m), 8.57 (2H, br m), 8.65 (2H, d), 8.98 (1H, d), 9.44(1H, d).

Workup

  1. customat 140° C.
  2. customfor 15 minutes
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with more ethanol

Sources & evidence

ORD record
ord-4f345c5b07f94cb9a328d49b295f2dbc
Source dataset
uspto-grants-2009_05
Patent number
US07528138B2

Reaction notes

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