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2-Amino-4,6-dimethoxypyrimidine → 4-(Cyclopropylcarbonyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-methyl-1H-pyrazole-5-sulfonamide

HRID 231405
Notes
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Reaction equation

HRID 231405 reaction equation
[CH:1]1([C:4]([C:6]2[CH:7]=[N:8][N:9]([CH3:15])[C:10]=2[S:11]([NH2:14])(=[O:13])=[O:12])=[O:5])[CH2:3][CH2:2]1.C1(N[C:23](=O)[O-:24])C=CC=CC=1.[CH3:26][O:27][C:28]1[CH:33]=[C:32]([O:34][CH3:35])[N:31]=[C:30]([NH2:36])[N:29]=1.[N+](=C1CCCCCCCCCC1C1CCCCCCCCCC1)=[N-]>C(#N)C>[CH:1]1([C:4]([C:6]2[CH:7]=[N:8][N:9]([CH3:15])[C:10]=2[S:11]([NH:14][C:23]([NH:36][C:30]2[N:31]=[C:32]([O:34][CH3:35])[CH:33]=[C:28]([O:27][CH3:26])[N:29]=2)=[O:24])(=[O:13])=[O:12])=[O:5])[CH2:2][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 142309984-Cyclopropylcarbonyl-1-methyl-5-pyrazolesulfonamideHCID 21896570PhenylcarbamateHCID 22171225Diazobicycloundecane

Product 1

HCID 142309994-(Cyclopropylcarbonyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-methyl-1H-pyrazole-5-sulfonamide

Reagents, catalysts & solvents

1
HCID 6342AcetonitrileSolvent

Procedure

To a stirring mixture of the sulfonamide from Example 2 (175 mg, 0.76 mmol) and the phenylcarbamate of 4,6-dimethoxy-2-aminopyrimidine (210 mg, 0.76 mmol) in 3 ml of acetonitrile was added diazobicycloundecane (116 mg, 0.76 mmol). The solution was stirred for approximately 10 minutes. Acidification of the reaction mixture and filtration of the resulting solids afforded 300 mg of the desired compound m.p. 189°-192° C. NMR (200 MHz, CDCl3) 1.0 (m, 2H), 1.1 (m, 2H), 2.4 (m, 1H), 4.0 (s, 6H), 4.35 (s, 1H), 5.80 (s, 1H), 7.4 (br. s, 1H), 8.05 (s, 1H), 12.9 (s, 1H).

Workup

  1. filtrationAcidification of the reaction mixture and filtration of the resulting solids

Sources & evidence

ORD record
ord-5b8f307d02064ce6995a15186cec2310
Source dataset
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04846878

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes