Sodium Carbonate → (6-(3,4-Dichlorophenylamino)pyrimidin-4-yl)methanol

HRID 77470Notes

Reaction equation

HRID 77470 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:7]=[C:8]([NH:13][C:14]2[CH:19]=[C:18]([CH2:20][O:21]C)[N:17]=[CH:16][N:15]=2)[CH:9]=[CH:10][C:11]=1[Cl:12].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]([NH:13][C:14]2[N:15]=[CH:16][N:17]=[C:18]([CH2:20][OH:21])[CH:19]=2)[CH:9]=[CH:10][C:11]=1[Cl:12]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 86679758HCID 86679758, compound

Product 1

HCID 86679759(6-(3,4-Dichlorophenylamino)pyrimidin-4-yl)methanolYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (0.399 ml, 4.22 mmol) was added dropwise to a stirred solution of N-(3,4-dichlorophenyl)-6-(methoxymethyl)pyrimidin-4-amine (0.3 g, 1.056 mmol) in DCM (4.0 mL) at 0° C. The mixture was further stirred for 30 min and poured onto ice water. The pH was adjusted to 10 using sat. Na2CO3 solution. The resulting suspension was extracted with ethyl acetate. The organic layer was isolated and dried over K2CO3 and concentrated to give (6-(3,4-dichlorophenylamino)pyrimidin-4-yl)methanol as a brown solid (0.275 g, 96%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.05 (1H, br. s.), 8.92 (1H, s), 8.14 (1H, s), 7.71 (1H, d, J=8.78 Hz), 7.60 (1H, dd, J=8.78, 2.51 Hz), 7.05 (1H, s), 4.60 (2H, s). LCMS: R.T.=2.88; [M+H]+=271.96.

Workup

  1. additionpoured onto ice water
  2. extractionThe resulting suspension was extracted with ethyl acetate
  3. customThe organic layer was isolated
  4. dry with materialdried over K2CO3
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7571d02d09c14568b7f8482346396014
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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