Diisopropylethylamine → HCID 178493093, compound

HRID 1641390Notes

Reaction equation

HRID 1641390 reaction equation
ClC1N=C(NC2C=C(OC)NN=2)C(Cl)=CN=1.[Cl:17][C:18]1[C:19]([NH:34][C:35]2[CH:39]=[C:38]([O:40][CH:41](C)C)[NH:37][N:36]=2)=[N:20][C:21]([NH:24][C@H:25]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][N:28]=2)[CH3:26])=[N:22][CH:23]=1.CCN(C(C)C)C(C)C>CCCCO>[Cl:17][C:18]1[C:19]([NH:34][C:35]2[CH:39]=[C:38]([O:40][CH3:41])[NH:37][N:36]=2)=[N:20][C:21]([NH:24][C@H:25]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][N:28]=2)[CH3:26])=[N:22][CH:23]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 178458654HCID 178458654, compoundHCID 1784930722,5-dichloro-N-(5-methoxy-1H-pyrazol-3-yl)pyrimidin-4-amine

Product 1

HCID 178493093HCID 178493093, compoundYield 144%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

2,5-Dichloro-N-(5-methoxy-1H-pyrazol-3-yl)pyrimidin-4-amine (Method 37; 0.25 mmol, 64 mg) and (1S)-1-(5-fluoropyridin-2-yl)ethanamine (Method 6; 0.25 mmol, 34.5 mg) were dissolved in n-BuOH (0.35 M) and DIEA (0.50 mmol, 0.08 ml) was added. The reaction was stirred at 110° C. overnight. The solvent was evaporated and the remaining material was separated between EtOAc and water, washed with brine, and dried. Evaporation of the solvent gave a brown oil (131 mg). This material was purified by Gilson (10-50% acetonitrile/H2O, 15 min). The title compound was collected by evaporation of the solvent as a white solid (2.3 mg). 1H NMR (MeOD) 8.32 (d, 1H), 7.85-8.07 (m, 1H), 7.49 (ddd, 1H), 7.29-7.41 (m, 1H), 5.80 (s, 1H), 4.92-5.19 (m, 1H), 3.82 (s, 3H), 1.50 (d, 3H); m/z 364.

Workup

  1. customThe solvent was evaporated
  2. customthe remaining material was separated between EtOAc and water
  3. washwashed with brine
  4. customdried
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c66bd9c4042044afbcb5af813fe022b8
Source dataset
uspto-grants-2012_02
Patent number
US08114989B2

Reaction notes

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