Boron tribromide → HCID 18763621, compound

HRID 431250Notes

Reaction equation

HRID 431250 reaction equation
C[O:2][C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[C:11]2[N:16]=[C:15]([CH3:17])[CH:14]=[C:13]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:12]=2)[CH:6]=[CH:7][CH:8]=1.ClC1C=C(C)N=C(/C=C/C2C=CC=C(OC)C=2)N=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[C:11]2[N:16]=[C:15]([CH3:17])[CH:14]=[C:13]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:12]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 9965957HCID 9965957, compoundHCID 18763668HCID 18763668, compound

Product 1

HCID 18763621HCID 18763621, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (E)-2-[2-(3-methoxy-phenyl)-vinyl]-4-methyl-6-pyrrolidin-1-yl-pyrimidine (100 mg, 0.34 mmol), product of example 29, in CH2Cl2 there was added dropwise and under stirring at 0° C. a 1M solution of BBr3 in CH2Cl2 (0.51 ml). The reaction mixture was stirred for 1 h at 0° C. after which time the reaction was complete according to TLC analysis. The mixture was poured on ice and the product extracted into CH2Cl2. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crystalline solid which formed was filted off by suction and dried in a high vacuum to give (E)-2-[2-(3-hydroxy-phenyl)-vinyl]-4-methyl-6-pyrrolidin-1-yl-pyrimidine (45 mg, 47.2%) as a light grey solid. ISP mass spectrum, m/e: 282.2 (M+1 calculated for C17H19N3O: 282).

Workup

  1. additionThe mixture was poured on ice
  2. extractionthe product extracted into CH2Cl2
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crystalline solid which formed
  6. customdried in a high vacuum

Sources & evidence

ORD record
ord-dd5ea18242934ad49c7ac616702778e4
Source dataset
uspto-grants-2003_12
Patent number
US06657060B2

Reaction notes

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