Sodium Hydroxide → HCID 14306132, compound

HRID 867876Notes

Reaction equation

HRID 867876 reaction equation
B(Br)(Br)Br.C[O:6][CH2:7][C:8]1[N:13]=[C:12]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:11]=[CH:10][N:9]=1.[OH-].[Na+]>ClCCl>[OH:6][CH2:7][C:8]1[N:13]=[C:12]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 14306131HCID 14306131, compound

Product 1

HCID 14306132HCID 14306132, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (6.1 ml) was added dropwise to a stirred solution of 2-methoxymethyl-4-piperidinopyrimidine (3.35 g) in dichloromethane (60 ml) at 0°-5° under nitrogen. After a further 30 minutes the mixture was poured onto ice, the pH raised to 13 (NaOH) and extracted with chloroform. The combined extracts were dried (K2CO3) and the volume reduced. Ether was added to give 2-hydroxymethyl-4-piperidino-pyrimidine (2.78 g) as a crystalline solid, m.p. 92°-3°.

Workup

  1. additionAfter a further 30 minutes the mixture was poured onto ice
  2. extractionextracted with chloroform
  3. dry with materialThe combined extracts were dried (K2CO3)
  4. additionEther was added

Sources & evidence

ORD record
ord-01776aac310f4150985e9f039c00c48d
Source dataset
uspto-grants-1988_10
Patent number
US04777172

Reaction notes

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