Ethyl 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate → HCID 178469689, compound

HRID 1956446Notes

Reaction equation

HRID 1956446 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:15])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[NH2:21][C:22]1[C:23]([OH:29])=[N:24][C:25]([OH:28])=[N:26][CH:27]=1>>[OH2:12].[OH2:28].[ClH:1].[OH:28][C:25]1[N:24]=[C:23]([OH:29])[C:22]([NH:21][C:2]2[C:11]3[C:6](=[N:7][C:8]([CH3:15])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:27][N:26]=1.[CH2:19]([O:18][C:16]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:21][C:22]1[C:23]([OH:29])=[N:24][C:25]([OH:28])=[N:26][CH:27]=1)=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[C:8]([CH3:15])[N:7]=2)=[O:17])[CH3:20].[OH2:12].[OH2:12]

Participants

3

Reactant 2

HCID 23198600Ethyl 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylateHCID 178508041HCID 178508041, compound

Product 1

HCID 178469689HCID 178469689, compound

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate (2.0 g), 5-aminopyrimidine-2,4-diol (0.86 g) and IMS (25 ml) was boiled under reflux for 3 hours. The mixture was concentrated to approximately 15 ml, then cooled at 0° C. The mixture was filtered to give ethyl 4-(2,4-dihydroxy-5-pyrimidinylamino)-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate hemihydrochloride dihydrate, m.p. 250° C. Active (1/1) at 30 mg/kg.

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationThe mixture was concentrated to approximately 15 ml
  3. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-73ab87c84956483bb77a3e8fdea28379
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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