Solketal → HCID 68181687, compound

HRID 1398670Notes

Reaction equation

HRID 1398670 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:16][C:17]1[CH:18]=[CH:19][C:20]2[N:24]=[C:23](C(Cl)(Cl)Cl)[N:22]([C:29]3[CH:34]=[CH:33][N:32]=[C:31]([NH2:35])[N:30]=3)[C:21]=2[CH:36]=1>CN(C)C=O>[Br:16][C:17]1[CH:18]=[CH:19][C:20]2[N:24]=[C:23]([O:8][CH2:7][CH:5]3[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]3)[N:22]([C:29]3[CH:34]=[CH:33][N:32]=[C:31]([NH2:35])[N:30]=3)[C:21]=2[CH:36]=1

Participants

5

Reactant 3

HCID 7528SolketalHCID 10796Cesium carbonateHCID 681818334-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Product 1

HCID 68181687HCID 68181687, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2,2-dimethyl-1,3-dioxolan-4-yl)methanol (800 mg, 6.05 mmol), cesium carbonate (1.7 g, 5.22 mmol) and 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (500 mg, 1.23 mmol) in N,N-dimethylformamide (4 mL) was stirred for 12 hr at room temperature. The reaction mixture was quenched with 20 mL of water and the precipitate was collected by filtration. The solid was dried in a vacuum oven to afford 385 mg (75%) of 4-[6-bromo-2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 8.40 (d, J=5.2 Hz, 2H), 7.40 (s, 2H), 7.21 (d, J=6.0 Hz, 1H), 5.28 (s, 2H), 4.77-4.60 (m, 3H), 4.22-4.20 (m, 1H), 3.96-3.92 (m, 1H), 1.49 (s, 3H), 1.42 (s, 3H); LC-MS: m/z=+420 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with 20 mL of water
  2. filtrationthe precipitate was collected by filtration
  3. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-af374e2a10774102976194ca6c95237f
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

Loading…