Water → HCID 79639336, compound

HRID 1687207Notes

Reaction equation

HRID 1687207 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[O:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1.O>O1CCCC1.ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([NH:26][C:25]2[CH:24]=[CH:23][C:22]([N:19]3[CH2:20][CH2:21][O:16][CH2:17][CH2:18]3)=[CH:28][CH:27]=2)[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 79639336HCID 79639336, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,4,5-Trichloropyrimidine (1.05 g, 5.73 mmol) was dissolved in tetrahydrofuran (30 mL). Potassium carbonate (1.18 g, 8.55 mmol) was added, followed by 4-morpholinoaniline (1.017 g, 5.71 mmol). After stirring overnight, water (30 mL) and dichloromethane (30 mL) were added, the phases separated and the aqueous layer extracted once with dichloromethane (30 mL). The combined organic fractions were dried over sodium sulfate, concentrated onto silica gel and chromatographed (120 g SiO2, 0-60% EA:Hex). (2,5-Dichloro-pyrimidin-4-yl)-(4-morpholin-4-yl-phenyl)-amine was isolated as a yellow solid (1.29 g, 70%). m.p.=168-172° C.; LCMS (m/e) 325 (M+1); 1H-NMR (DMSO-d6, 400 MHz) δ 9.38 (s, 1H), 8.30 (s, 1H), 7.37 (d, 2H, J=9.0 Hz), 6.96 (d, 2H, J=9.0 Hz), 3.74 (t, 4H, J=4.9 Hz), 3.11 (t, 4H, J=4.9 Hz).

Workup

  1. customthe phases separated
  2. extractionthe aqueous layer extracted once with dichloromethane (30 mL)
  3. dry with materialThe combined organic fractions were dried over sodium sulfate
  4. concentrationconcentrated onto silica gel
  5. customchromatographed (120 g SiO2, 0-60% EA:Hex)

Sources & evidence

ORD record
ord-e208a2bbe56241b9b50e6b524eee9e49
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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