Formaldehyde → HCID 46785354, compound

HRID 2413170Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:5][N:6]([CH3:8])[CH3:7].[Mg].[CH2:15]=[O:16]>>[CH3:7][N:6]([CH2:5][C:4]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:2]([CH:3]=1)[CH2:15][OH:16])[CH3:8]

Participants

Reactant 3

HCID 712Formaldehyde

HCID 5462224Magnesium

HCID 204305213-Bromo-4-methoxy-N,N-dimethylbenzenemethanamine

Product 1

HCID 46785354HCID 46785354, compound

Procedure

Successive reaction of 3-bromo-4-methoxy-N,N-dimethylbenzylamine with magnesium and formaldehyde (in a similar manner to Example 7) gave 5-dimethylaminomethyl-2-methoxybenzyl alcohol, m.p. 67°-69°, which was heated under reflux for 4 hours with cysteamine hydrochloride in acetic acid to give, after basification and chloroform extraction, 2-(5-dimethylaminomethyl-2-methoxybenzylthio)ethylamine, as an oil. This oil was heated under reflux with 1.1 molar equivalents of 2-nitroamino-5-(3-pyridylmethyl)-4-pyrimidone in ethanol for 28 hours to give 2-[2-(5-dimethylaminomethyl-2-methoxybenzylthio)-ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone which was treated with hydrogen chloride in ethanol and purified as the trihydrochloride salt m.p. 232°-235° (recrystallised from methanol-ethanol).

Sources & evidence

ORD record: ord-d880481a049c45e49188c54059e4fc5b
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04496567

Reaction notes

Loading…