Methanol → 1-{1-[4-(3-phenyl-5-pyrimidin-2-ylpyridin-2-yl)benzyl]piperidin-4-yl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 2105528Notes

Reaction equation

HRID 2105528 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:11][C:10]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:5][CH:4]=1.[NH:27]1[CH2:32][CH2:31][CH:30]([N:33]2[C:37]3=[N:38][CH:39]=[N:40][C:41]([NH2:42])=[C:36]3[CH:35]=[N:34]2)[CH2:29][CH2:28]1.CCN(C(C)C)C(C)C.CO>C1COCC1>[C:21]1([C:10]2[C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH2:2][N:27]4[CH2:32][CH2:31][CH:30]([N:33]5[C:37]6=[N:38][CH:39]=[N:40][C:41]([NH2:42])=[C:36]6[CH:35]=[N:34]5)[CH2:29][CH2:28]4)=[CH:8][CH:7]=3)=[N:14][CH:13]=[C:12]([C:15]3[N:16]=[CH:17][CH:18]=[CH:19][N:20]=3)[CH:11]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 577139461-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidin-4-amineHCID 578085322-{6-[4-(Bromomethyl)phenyl]-5-phenylpyridin-3-yl}pyrimidine

Product 1

HCID 111919341-{1-[4-(3-phenyl-5-pyrimidin-2-ylpyridin-2-yl)benzyl]piperidin-4-yl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of crude 2-{6-[4-(bromomethyl)phenyl]-5-phenylpyridin-3-yl}pyrimidine (0.050 g, 0.124 mmol), 1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.030 g, 0.137 mmol), and DIEA (0.065 mL, 0.373 mmol) in 1:1 MeOH:THF (1 mL) was stirred for 1 hr. Reaction concentrated and the residue was purified by reverse phase HPLC (5% CH3CN: 95% H2O: 0.01% TFA to 95% CH3CN: 5% H2O: 0.01% TFA) to give the title compound. 1H-NMR (500 MHz, d6 DMSO) δ 9.77 (bs, 1H), 9.60 (d, 1H, J=2.0 Hz), 9.00 (d, 2H, J=4.9 Hz), 8.70 (bs, 1H), 8.68 (d, 2H, J=2.0 Hz), 8.45 (bs, 1H), 8.37 (s, 1H), 8.30 (s, 1H), 7.58 (t, 1H, J=4.9 Hz), 7.54-7.37 (m, 9H), 5.05-4.93 (m, 1H), 4.35 (s, 2H), 3.49 (d, 2H, J=11.23 Hz), 3.37-3.21 (m, 2H), 2.47-2.33 (m, 2H), 2.15 (d, 2H, J=11.7 Hz) HRMS m/z (M+H) Calcd: 540.2619, found: 540.2616.

Workup

  1. customReaction
  2. concentrationconcentrated
  3. customthe residue was purified by reverse phase HPLC (5% CH3CN: 95% H2O: 0.01% TFA to 95% CH3CN: 5% H2O: 0.01% TFA)

Sources & evidence

ORD record
ord-00b79e8efde4484c866729d7c3e7999f
Source dataset
uspto-grants-2009_08
Patent number
US07579355B2

Reaction notes

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