Hydrochloric Acid → HCID 89924137, compound

HRID 1752653

Reaction equation

HRID 1752653 reaction equation
[Br:1][C:2]1[N:7]=[C:6](Br)[CH:5]=[CH:4][N:3]=1.[O:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH2:11][CH2:10]1.Cl.CCN(C(C)C)C(C)C>C(O)C.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[N:7]=[C:6]([N:18]2[CH2:17][CH2:16][N:15]([CH:12]3[CH2:13][CH2:14][O:9][CH2:10][CH2:11]3)[CH2:20][CH2:19]2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 149763012,4-DibromopyrimidineHCID 219423151-(Oxan-4-yl)piperazine

Product 1

HCID 89924137HCID 89924137, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Procedure

A solution of 2,4-dibromopyrimidine (50 mg, 0.210 mmol) and 1-(tetrahydro-2H-pyran-4-yl)piperazine, 2 Hydrochloride (51.1 mg, 0.210 mmol) in Ethanol (1 mL) was treated with DIPEA (0.147 mL, 0.841 mmol) and DMAP (cat.) and stirred at ambient temperature for 1 h. The reaction mixture was concentrated in vacuo and triturated with water, filtered and the solid washed with water then dried in vacuo to provide 2-bromo-4-(4-(tetrahydro-2H-pyran-4-yl)piperazin-1-yl)pyrimidine (43 mg, 0.130 mmol, 61.9% yield) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.54 (s, 2H) 1.73 (br. s., 2H) 2.48 (br. s., 1H) 2.61 (br. s., 4H) 3.38 (t, J=11.24 Hz, 2H) 3.65 (br. s., 4H) 4.02 (br. s., 2H) 6.40 (d, J=6.25 Hz, 1H) 7.95 (d, J=5.86 Hz, 1H). LC/MS (m/z) ES+=327 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customtriturated with water
  3. filtrationfiltered
  4. washthe solid washed with water
  5. customthen dried in vacuo

Sources & evidence

ORD record
ord-13732ee95e3e4e478546b28b048589f0
Source dataset
uspto-grants-2015_10
Patent number
US09163023B2

Linked notes

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