Diisopropylethylamine → N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-(pyridin-2-ylmethoxy)pyrimidine-5-carboxamide

HRID 403043Notes

Reaction equation

HRID 403043 reaction equation
CS[C:3]1[N:8]=[CH:7][C:6]([C:9]([OH:11])=O)=[CH:5][N:4]=1.[NH2:12][C:13]1[CH:14]=[C:15]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:16]([NH:18][CH:19]1[CH2:21][CH2:20]1)=[O:17].CN(C(ON1N=N[C:36]2[CH:37]=[CH:38][CH:39]=[N:40][C:35]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:59](=O)(O)[O-:60].[Na+]>CN(C=O)C>[CH:19]1([NH:18][C:16]([C:15]2[CH:22]=[CH:23][C:24]([CH3:25])=[C:13]([NH:12][C:9]([C:6]3[CH:7]=[N:8][C:3]([O:60][CH2:59][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][N:40]=4)=[N:4][CH:5]=3)=[O:11])[CH:14]=2)=[O:17])[CH2:20][CH2:21]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 36317942-(Methylthio)pyrimidine-5-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 119838543-amino-N-cyclopropyl-4-methylbenzamide

Product 1

HCID 11475163N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-(pyridin-2-ylmethoxy)pyrimidine-5-carboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(methylthio)pyrimidine-5-carboxylic acid (1.50 g, 8.82 mmol) and 3-amino-N-cyclopropyl-4-methylbenzamide (1.68 g, 8.82 mmol) in DMF (7.5 mL) was added HATU (3.69 g, 9.70 mmol) and DIPEA (4.30 mL, 26.46 mmol) and the resulting mixture stirred for 16 h at room temperature. Saturated aqueous sodium bicarbonate was added and the mixture extracted with ethyl acetate, washed with brine and concentrated under reduced pressure to give the title compound as a solid (3.04 g, 100%); NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.69 (m, 2H), 2.28 (s, 3H), 2.60 (s, 3H), 2.86 (m, 1H), 7.36 (m, 1H), 7.65 (m, 1H), 7.85 (m, 1H), 8.39 (m, 1H), 9.12 (s, 2H), 10.18 (m, 1H); Mass Spectrum: M−H′ 341.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washwashed with brine
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e5debcd4cc741d9b6492d857a7c13e6
Source dataset
uspto-grants-2014_06
Patent number
US08742124B2

Reaction notes

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