Heptane → N-Methyl-4-{4-phenyl-1-[1-(pyrimidin-2-ylmethyl)piperidin-4-yl]-1H-imidazol-5-yl}pyrimidin-2-amine

HRID 1896664Notes

Reaction equation

HRID 1896664 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[N:13]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:12]=[N:11][C:10]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][N:4]=1.Cl[CH2:27][C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1.FC1C=CC(C2N=CN(C3CCN(CC4N=CC=CN=4)CC3)C=2C2C=CN=C(N)N=2)=CC=1.CCCCCCC>ClCCl.O>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[N:13]([CH:14]3[CH2:15][CH2:16][N:17]([CH2:27][C:28]4[N:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:18][CH2:19]3)[CH:12]=[N:11][C:10]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 8900HeptaneHCID 128773712-(Chloromethyl)pyrimidineHCID 574617294-{4-(4-Fluorophenyl)-1-[1-(pyrimidin-2-ylmethyl)piperidin-4-yl]-1H-imidazol-5-yl}pyrimidin-2-amineHCID 58235131HCID 58235131, compound

Product 1

HCID 58235122N-Methyl-4-{4-phenyl-1-[1-(pyrimidin-2-ylmethyl)piperidin-4-yl]-1H-imidazol-5-yl}pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

The title product was prepared by reaction of N-methyl-4-(4-phenyl-1-piperidin-4-yl-1H-imidazol-5-yl)pyrimidin-2-amine (C26) with 2-(chloromethyl)-pyrimidine according to the general procedure for the synthesis of 4-{4-(4-fluorophenyl)-1-[1-(pyrimidin-2-ylmethyl)piperidin-4-yl]-1H-imidazol-5-yl}pyrimidin-2-amine (3) in Example 3. In this case, after the reaction cooled to room temperature, it was diluted with dichloromethane (20 mL) and water (2 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to provide a light yellow solid, which was dissolved in a small volume of dichloromethane. Addition of heptane caused a solid to precipitate; this mixture was stirred for 30 minutes and then the solid was collected by filtration, washed with heptane and washed with diethyl ether to provide the product as a light yellow solid. Yield: 106 mg, 0.248 mmol, 34%. APCI m/z 427.1 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.12-2.17 (m, 4H), 2.29-2.36 (m, 2H), 2.97 (s, 3H), 3.11 (br d, J=12 Hz, 2H), 3.85 (s, 2H), 4.74 (br s, 1H), 6.34 (d, J=5.1 Hz, 1H), 7.29-7.35 (m, 3H), 7.38-7.43 (m, 3H), 8.06 (s, 1H), 8.09 (br d, J=5 Hz, 1H), 8.80 (d, J=4.9 Hz, 2H).

Workup

  1. dry with materialThe organic layer was dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customto provide a light yellow solid, which
  5. customto precipitate
  6. filtrationthe solid was collected by filtration
  7. washwashed with heptane
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-0724ee0a385543c1a871cd78eed43e10
Source dataset
uspto-grants-2013_08
Patent number
US08518944B2

Reaction notes

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