Boron tribromide → Isobutyl 1-(2-(2-hydroxyphenyl)thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylcarbamate

HRID 333704Notes

Reaction equation

HRID 333704 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[C:11]([N:18]2[CH2:23][CH2:22][CH:21]([NH:24][C:25](=[O:31])[O:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:20][CH2:19]2)[C:12]2[S:17][CH:16]=[CH:15][C:13]=2[N:14]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[C:11]([N:18]2[CH2:19][CH2:20][CH:21]([NH:24][C:25](=[O:31])[O:26][CH2:27][CH:28]([CH3:29])[CH3:30])[CH2:22][CH2:23]2)[C:12]2[S:17][CH:16]=[CH:15][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59026634Isobutyl 1-(2-(2-methoxyphenyl)thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylcarbamate

Product 1

HCID 135581751Isobutyl 1-(2-(2-hydroxyphenyl)thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of isobutyl 1-(2-(2-methoxyphenyl)thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylcarbamate (0.13 g, 0.30 mmol) in CH2Cl2 (2 mL) was cooled to −50° C., and a solution of BBr3 in CH2Cl2 (1 M, 1.8 mL, 1.8 mmol) was slowly added. The reaction was allowed to gradually warm to room temperature over 3 h, and saturated aqueous NaHCO3 was slowly added. The organic layer was separated, washed with water, dried over Na2SO4, and concentrated under vacuum. The residue was purified by preparative reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) to give isobutyl 1-(2-(2-hydroxyphenyl)thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylcarbamate. LC/MS: m/z 427.3 (M+H)+ at 3.08 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by preparative reverse phase

Sources & evidence

ORD record
ord-10f6ca12ad2f461ca87837a7cd4aef2e
Source dataset
uspto-grants-2014_11
Patent number
US08883781B2

Reaction notes

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