Cyclohexylamine → HCID 58317571, compound

HRID 515969Notes

Reaction equation

HRID 515969 reaction equation
C([C:3]1[N:8]=[C:7]([C:9]#[N:10])[C:6]([C:11]([O:13][CH3:14])=[O:12])=[C:5]([NH:15][C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)[N:4]=1)#N.C(N(CC)C(C)C)(C)C.[CH:32]1([NH2:38])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:9]([C:7]1[C:6]([C:11]([O:13][CH3:14])=[O:12])=[C:5]([NH:15][C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)[N:4]=[C:3]([NH:38][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[N:8]=1)#[N:10]

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 58317584HCID 58317584, compound

Product 1

HCID 58317571HCID 58317571, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2,4-dicyano-6-(m-tolylamino)pyrimidine-5-carboxylate (102.3 mg, 0.349 mmol), N,N-diisopropylethylamine (0.075 mL, 0.429 mmol) and cyclohexylamine (0.05 mL, 0.437 mmol) in DMF (2 mL) was stirred at RT for 14 h. Saturated aq NaHCO3 was added and the mixture was extracted with EtOAc. The organic layers were washed with aq NaHCO3, water, and brine, and were filtered through SiO2. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (SiO2, hexanes/EtOAc=4/1) to give the title compound as a yellow oil (114.7 mg, 90%). 1H NMR (500 MHz, CDCl3) δ ppm 1.19-1.45 (m, 5H), 1.64-1.67 (m, 1H), 1.73-1.80 (m, 2H), 2.00-2.05 (m, 2H), 2.38 (s, 3H), 3.75-3.82 (m, 1H), 3.98 (s, 3H), 5.57-5.58 (br d, J=7.9 Hz, 1H), 6.97-6.98 (m, 1H), 7.27-7.29 (m, 1H), 7.46-7.51 (m, 2H), 10.62 (br s, 1H). [M+H] calc'd for C20H24N5O2, 366; found, 366.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic layers were washed with aq NaHCO3, water, and brine
  3. filtrationwere filtered through SiO2
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography (SiO2, hexanes/EtOAc=4/1)

Sources & evidence

ORD record
ord-3c27251e10ab4167b3d6c48096c44331
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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