Boron tribromide → HCID 67297993, compound

HRID 1520386Notes

Reaction equation

HRID 1520386 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[C:14]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[N:13]=[C:12]3[NH:25][CH3:26])[CH:6]=[CH:7][CH:8]=1.COC1C=C(C2C=C3C(=CC=2)N=C(C2C=NC=CC=2)N=C3N2CCCC2)C=CC=1.N1CCCC1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:26][NH:25][C:12]1[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([C:5]3[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=3)[CH:10]=2)[N:15]=[C:14]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[N:13]=1

Participants

7

Reactant 5

HCID 25134Boron tribromideHCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 67298122HCID 67298122, compoundHCID 67298534HCID 67298534, compound

Product 1

HCID 67297993HCID 67297993, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 6-(3-methoxyphenyl)-N-methyl-2-(pyridin-3-yl)quinazolin-4-amine (prepared in a similar method described for 6-(3-methoxy phenyl)-2-(pyridine-3-yl)-4-(pyrrolidin-1-yl)quinazoline using Scheme 74, substituting N-methylamine for pyrrolidine) (1.00 g, 2.9 mmol) in CH2Cl2 (15 mL) and boron tribromide 1M solution in dichloromethane (8.76 ml, 8.76 mmol) was added at 0° C. The reaction mixture was stirred overnight at room temperature after which it was carefully poured into a vigorously stirring mixture of ice and saturated aqueous solution of NaHCO3. The resultant solid was collected by filtration, dried and then dissolved in a mixture of K2CO3 (2 g) and methanol (50 mL). The solution was then acidified using aqueous NH4Cl solution. (50 mL) and the precipitate which formed was collected by filtration and dried to give 0.95 g of 3-(4-(methylamino)-2-(pyridin-3-yl)quinazolin-6-yl)phenol as pale yellow solid (99%). LCMS m/z=329 (M+1) (Method D) (retention time=1.30 min). 1H NMR (300 MHz, DMSO) δ 9.63 (s, 1H), 9.60 (s, 1H), 8.77 (d, J=8.0 Hz, 1H), 8.74-8.59 (m, 2H), 8.54 (s, 1H), 8.05 (d, J=8.7 Hz, 1H), 7.83 (d, J=8.7 Hz, 1H), 7.54 (dd, J=7.9, 4.8 Hz, 1H), 7.38-7.12 (m, 3H), 6.82 (d, J=7.8 Hz, 1H), 3.17 (d, J=4.3 Hz, 3H).

Workup

  1. customprepared in a similar method
  2. additionwas carefully poured into
  3. stirringa vigorously stirring
  4. filtrationThe resultant solid was collected by filtration
  5. customdried
  6. dissolutiondissolved in a mixture of K2CO3 (2 g) and methanol (50 mL)
  7. custom(50 mL) and the precipitate which formed
  8. filtrationwas collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-77845764cbbb4a66a20227e5d6dd54ad
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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