Diisopropylethylamine → N-(4-Ethynylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 530963Notes

Reaction equation

HRID 530963 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[CH:10][C:11]([C:12]([OH:14])=O)=[C:4]2[N:3]=1.[C:15]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)#[CH:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:15]([C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:12]([C:11]2[CH:10]=[N:9][N:5]3[C:6]([CH3:8])=[CH:7][C:2]([CH3:1])=[N:3][C:4]=23)=[O:14])=[CH:19][CH:18]=1)#[CH:16]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 7440385,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 37600254-EthynylanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 46907762N-(4-Ethynylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxamideYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid (722 mg, 3.78 mmol), 4-ethynylaniline (442 mg, 3.78 mmol), and HATU (1436 mg, 3.78 mmol) were taken up in DMF (10 ml) and then treated with diisopropylethylamine (1.979 ml, 11.33 mmol). The contents stirred at room temperature overnight. The product had precipitated from reaction mixture. The reaction was diluted with water, filtered through a Büchner funnel under house vacuum. The residue was washed with water (×2), then CH2Cl2, diethyl ether, and air dried to obtain N-(4-ethynylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxamide (500 mg, 1.72 mmol, 46% yield). LC-MS: rt (min)=3.65. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.71 (s, 3H), 2.77 (s, 3H), 4.11 (s, 1H), 7.21 (s, 1H), 7.49 (d, J=8.6 Hz, 2H), 7.77 (d, J=8.6 Hz, 2H), 8.65 (s, 1H), 10.31 (s, 1H).

Workup

  1. customThe product had precipitated from reaction mixture
  2. additionThe reaction was diluted with water
  3. filtrationfiltered through a Büchner funnel under house vacuum
  4. washThe residue was washed with water (×2)
  5. dry with materialCH2Cl2, diethyl ether, and air dried

Sources & evidence

ORD record
ord-d69c47c3d9c1473abaa0ea5bdc4defae
Source dataset
uspto-grants-2016_05
Patent number
US09353117B2

Reaction notes

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