5-(3-Pyridylmethoxy)-2-thiouracil → 5-(4-Pyridylmethyl)-2-thiouracil

HRID 262508Notes

Reaction equation

HRID 262508 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](COCC(OCC)=O)[CH:2]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][C:23]2[C:24](=[O:30])[NH:25][C:26](=[S:29])[NH:27][CH:28]=2)[CH:16]=1.Cl[C:32]1[C:33]([CH2:38][S:39][CH2:40][CH2:41][NH:42][C:43]2NC(=S)[C:46](CC3C=NC=CC=3)=[CH:45][N:44]=2)=[N:34]C=CC=1>>[N:1]1[CH:2]=[CH:3][C:4]([CH2:32][C:23]2[C:24](=[O:30])[NH:25][C:26](=[S:29])[NH:27][CH:28]=2)=[CH:5][CH:6]=1.[CH3:46][C:45]1[NH:44][CH:43]=[N:42][C:41]=1[CH2:40][S:39][CH2:38][CH2:33][NH:34][C:26]1[NH:25][C:24](=[O:30])[C:23]([O:22][CH2:21][C:17]2[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=2)=[CH:28][N:27]=1

Participants

5

Reactant 3

HCID 133735255-(3-Pyridylmethoxy)-2-thiouracilHCID 19261392Ethyl 2-((pyridin-3-yl)methoxy)acetateHCID 233491502-[2-(3-Chloro-2-pyridylmethylthio)ethylamino]-5-(3-pyridylmethyl)pyrimid-4-thione

Product 2

HCID 143385795-(4-Pyridylmethyl)-2-thiouracilHCID 233492822-[2-(5-Methyl-4-imidazolylmethylthio)ethylamino]-5-(3-pyridylmethoxy)-4-pyrimidone

Procedure

Ethyl 3-pyridylmethoxyacetate is converted into 5-(3-pyridylmethoxy)-2-thiouracil by the general procedure of Example 1 (i). Substitution of 5-(3-pyridylmethoxy)-2-thiouracil for 5-(4-pyridylmethyl)-2-thiouracil in the general procedure of Example 1 gives 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(3-pyridylmethoxy)-4-pyrimidone.

Sources & evidence

ORD record
ord-d7871d97cc554e58b7caaffa09909b3d
Source dataset
uspto-grants-1979_05
Patent number
US04154834

Reaction notes

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