Diisopropylethylamine → HCID 68786687, compound

HRID 2401446Notes

Reaction equation

HRID 2401446 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[N:3]=1.C(N(C(C)C)C(C)C)C.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]>C(O)CC>[NH2:8][C:4]1[N:3]=[C:2]([NH:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2233322-Amino-4-chloropyrimidineHCID 2756543tert-butyl N-(3-aminopropyl)-N-methylcarbamate

Product 1

HCID 68786687HCID 68786687, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A solution of 4-chloropyrimidin-2-amine (CAS#3993-78-0, 0.200 g, 0.0015 mole), N-ethyl-N-isopropylpropan-2-amine (1.88 mL, 0.0108 mole), and tert-butyl 3-aminopropyl(methyl)carbamate (0.300 g, 0.0015 mole) in n-propanol (3 mL) was heated at 200° C. under microwave irradiation for 10 minutes. Volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel eluting with 97:3:trace DCM/MeOH/aq. NH4OH. Two major products were isolated. The first product to elute was the isomeric byproduct, tert-butyl 3-((2-aminopyrimidin-4-yl)(methyl)amino)propylcarbamate. The second product to elute was the desired product, tert-butyl 3-(2-aminopyrimidin-4-ylamino)propyl(methyl)carbamate (0.040 g, 9.2%). 1H NMR (300 MHz, CD3OD) δ ppm 1.43 (s, 9H), 1.79 (pentet, J=7 Hz, 2H), 2.86 (s, 3H), 3.26-3.33 (m, 4H), 5.81 (d, J=6 Hz, 1H), 7.58 (d, J=6 Hz, 1H). MS (DCl—NH3) m/z=282 (M+H)+.

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel eluting with 97:3
  7. customTwo major products were isolated
  8. washThe first product to elute
  9. washThe second product to elute

Sources & evidence

ORD record
ord-8857a70428174b8cb18d4a2484188137
Source dataset
uspto-grants-2014_08
Patent number
US08796297B2

Reaction notes

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