Sodium Hydroxide → HCID 13068466, compound

HRID 1759131Notes

Reaction equation

HRID 1759131 reaction equation
O[C:2]1[C:3]2[CH2:11][CH2:10][O:9][C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1.NC1N=C([Cl:19])C(CCCl)=C(Cl)N=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>>[Cl:19][C:2]1[C:3]2[CH2:11][CH2:10][O:9][C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 13068465HCID 13068465, compoundHCID 178508904HCID 178508904, compound

Product 1

HCID 13068466HCID 13068466, compound

Procedure

5,6-Dihydro-4-hydroxyfuro[2,3-d]pyrimidine-2-amine [Svab, Budesinski and Vavrina, Collection Czech. Chem. Commun. 32, 1582 (1967)] can be converted to 2-amino-5-(2-chloroethyl)-4,6-dichloropyrimidine by heating with phosphorus oxychloride. The product can be subsequently cyclized by treatment with two equivalents of aqueous sodium hydroxide to afford 4-chloro-5,6-dihydrofuro[2,3-d]pyrimidin-2-amine, which is then converted to 5,6-dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-amine by heating with excess sodium methoxide in methanol. ##STR38##

Sources & evidence

ORD record
ord-f21f923f3e3a46d3888d5be970aa1a38
Source dataset
uspto-grants-1982_07
Patent number
US04339267

Reaction notes

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