Sodium Iodide → [4-(5-Bromo-pyrimidin-2-ylamino)-phenyl]-methanol

HRID 2067867Notes

Reaction equation

HRID 2067867 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:12]=[N:13][C:14](Cl)=[N:15][CH:16]=1.[I-].[Na+].C(N(C(C)C)CC)(C)C>CC(O)C>[Br:10][C:11]1[CH:12]=[N:13][C:14]([NH:1][C:2]2[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=2)=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 693314-Aminobenzyl alcoholHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 57632949[4-(5-Bromo-pyrimidin-2-ylamino)-phenyl]-methanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
200 °C

Procedure

To a solution of 4-aminobenzyl alcohol 14 (8.12 mmol) and 5-bromo-2-chloro-pyrimidine 4 (9.74 mmol) in 2-propanol (20 mL) is added sodium iodide (8.12 mmol) and diisopropylethylamine (16.2 mmol). The reaction mixture is heated in the microwave oven at 200° C. for 15 min. Purification by silica gel chromatography with hexane:EtOAc=7:3 affords [4-(5-bromo-pyrimidin-2-ylamino)-phenyl]-methanol 15. 1H NMR (400 MHz, CDCl3) δ 8.36 (s, 2H), 7.49 (d, J=8.8 Hz, 2H), 7.28 (d, J=8.4 Hz, 2H) 7.07 (bs, 1H), 4.60 (s, 2H). MS (m/z) (M+1)+: 280.3, 282.3.

Workup

  1. customPurification by silica gel chromatography with hexane

Sources & evidence

ORD record
ord-6aa99d33cff6418eb15c6f311ae1bc2f
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

Loading…