Boron tribromide → (6-Aminopyrimidin-4-yl)methanol

HRID 1241402Notes

Reaction equation

HRID 1241402 reaction equation
C[O:2][CH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([NH:10]C(=O)OC(C)(C)C)[CH:5]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:10][C:6]1[N:7]=[CH:8][N:9]=[C:4]([CH2:3][OH:2])[CH:5]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21934671Tert-butyl 6-(methoxymethyl)pyrimidin-4-ylcarbamate

Product 1

HCID 21934615(6-Aminopyrimidin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 6-(methoxymethyl)pyrimidin-4-ylcarbamate (100 mg, 0.42 mmole) in CH2Cl2 (2 mL) was added BBr3 (2.1 mL, 1M solution in CH2Cl2, 2.1 mmole) dropwise at −20° C. After 1.5 hours, the mixture was quenched with MeOH and concentrated. The solid was taken up in MeOH and concentrated (2×) and dried in vacuo to give the title compound as a tan solid. 1H-NMR (300 MHz, d6-DMSO) δ 8.63 (s, 1H), 6.64 (s, 1H), 4.50 (s, 2H).

Workup

  1. customthe mixture was quenched with MeOH
  2. concentrationconcentrated
  3. concentrationconcentrated (2×)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-04f85b49e491433799983b6d31883e50
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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