Sodium Hydroxide → 4-Pyrimidinemethanol,5-methyl-6-(1-piperidinyl)-

HRID 620166Notes

Reaction equation

HRID 620166 reaction equation
B(Br)(Br)Br.C[O:6][CH2:7][C:8]1[C:13]([CH3:14])=[C:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[N:11]=[CH:10][N:9]=1.[OH-].[Na+]>ClCCl>[OH:6][CH2:7][C:8]1[C:13]([CH3:14])=[C:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[N:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 143061614-Methoxymethyl-5-methyl-6-piperidinopyrimidine

Product 1

HCID 143061624-Pyrimidinemethanol,5-methyl-6-(1-piperidinyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (8.9 ml) in dichloromethane (25 ml) was added dropwise, under nitrogen, to a stirred solution of 4-methoxymethyl-5-methyl-6-piperidinopyrimidine (5 g) in dichloromethane (100 ml) at 0°-5°. After a further 2 hours the mixture was poured onto ice, the pH raised to 13 (NaOH) and extracted with chloroform. Extracts were dried (K2CO3) and stripped to a residue, which was triturated with diethyl ether to give 4-hydroxymethyl-5-methyl-6-piperidinopyrimidine, 3.80 g, as a crystalline solid, m.p. 79°-81°.

Workup

  1. additionAfter a further 2 hours the mixture was poured onto ice
  2. extractionextracted with chloroform
  3. dry with materialExtracts were dried (K2CO3)
  4. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-b81df03ca56840b8acb75dd4c0daeb51
Source dataset
uspto-grants-1989_04
Patent number
US04820708

Reaction notes

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