Diisopropylethylamine → HCID 68489584, compound

HRID 1641384Notes

Reaction equation

HRID 1641384 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:9]([NH2:11])[CH3:10])=[N:6][C:7]=1[CH3:8].Cl[C:13]1[N:18]=[C:17]([NH:19][C:20]2[CH:24]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[NH:22][N:21]=2)[C:16]([Cl:28])=[CH:15][N:14]=1.CCN(C(C)C)C(C)C>CCCCO>[Cl:28][C:16]1[C:17]([NH:19][C:20]2[CH:24]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[NH:22][N:21]=2)=[N:18][C:13]([NH:11][CH:9]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[C:7]([CH3:8])[N:6]=2)[CH3:10])=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 55293190HCID 55293190, compoundHCID 595867992,5-dichloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine

Product 1

HCID 68489584HCID 68489584, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
175 °C

Procedure

A microwave reaction vessel was charged with [1-(5-fluoro-6-methylpyridin-2-yl)ethyl]amine (Method 13; 159 mg, 1.03 mmol), 2,5-dichloro-4-(5-cyclopropyl-1H-pyrazole-3-ylamino)pyrimidine (Method 7; 335 mg, 1.24 mmol) and DIEA (0.35 ml, 2.0 mmol). Anhydrous n-BuOH (1.5 ml) was added, and the tube was sealed and heated in a microwave reactor at 175° C. for 10 hours. The resulting mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc, and the combined organics were washed with brine, dried, filtered, chromatography (Rf in 50:50 hexanes:EtOAc=0.25) to afford the title compound as a colourless solid (110 mg, 28%). 1H NMR (400 MHz, CDCl3) δ 0.65-0.75 (m, 2H), 0.85-0.95 (m, 2H), 1.47 (d, J=6.8 Hz, 3H), 1.82 (tt, J=8.5, 5.1 Hz, 1H), 2.46 (d, J=2.8 Hz, 3H), 4.99-5.09 (m, 1H), 6.01 (s, 1H), 6.26 (s, 1H), 7.05 (dd, J=8.3, 3.5 Hz, 1H), 7.15-7.23 (m, 1H), 7.38-7.48 (m, 1H), 7.84 (s, 1H). Calcd.: 387. Found [M+H+] 388.

Workup

  1. customA microwave reaction vessel
  2. customthe tube was sealed
  3. customThe resulting mixture was partitioned between EtOAc and H2O
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washthe combined organics were washed with brine
  6. customdried
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ba3a6f6979cf46fca84105113a484c07
Source dataset
uspto-grants-2012_02
Patent number
US08114989B2

Reaction notes

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