Triethylamine → 3-Methylthio-8-oxo-6-(2-cyclopropylmethoxyphenyl)-7,8-dihydropyrimido[4,5-e][1,2,4]triazine

HRID 728028Notes

Reaction equation

HRID 728028 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[N:5][C:6]([C:10]([O:12]CC)=O)=[C:7](Cl)[N:8]=1.Cl.[CH:16]1([O:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]([NH2:24])=[NH:23])[CH2:18][CH2:17]1.[CH2:29](N(CC)CC)C>>[CH3:1][S:2][C:3]1[N:4]=[N:5][C:6]2[C:10](=[O:12])[NH:24][C:22]([C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[O:19][CH2:16][CH:18]3[CH2:17][CH2:29]3)=[N:23][C:7]=2[N:8]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 11557703Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-CarboxylateHCID 224624062-Cyclopropoxybenzamidine hydrochloride

Product 1

HCID 1356707863-Methylthio-8-oxo-6-(2-cyclopropylmethoxyphenyl)-7,8-dihydropyrimido[4,5-e][1,2,4]triazineYield 59.8%

Procedure

In a similar manner to Example 18 reaction of 3-methylthio-5-chloro-6-carboethoxy-1,2,4-triazine (prepared from 3-methylthio-5-oxo-6-carboethoxy-4,5-dihydro-1,2,4-triazine, 1.5 g) with 2-cyclopropoxybenzamidine hydrochloride (2.35 g) and triethylamine (1.75 g) afforded a yellow solid (1.31g) which was recrystallised from acetonitrile and then from acetonitrile/ethanol (50%) to afford the title compound, 0.70 g, m.p. 235-236° C.

Sources & evidence

ORD record
ord-f08aef7edbee45f9aa5dfc1830b3c509
Source dataset
uspto-grants-1991_09
Patent number
US05047404

Reaction notes

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