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Sulfamic Acid → 6-(2,6-dichlorophenyl)-2-N-[3-(4-methylpiperazin-1-yl)propyl]pyrido[2,3-d]pyrimidine-2,7-diamine

HRID 3425
Notes
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Reaction equation

HRID 3425 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9]([NH2:20])=[N:8][C:6]=2[N:7]=1.S(=O)(=O)(O)N.N[CH2:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]1.C(=O)(O)[O-].[Na+]>O>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[C:10]1[C:9]([NH2:20])=[N:8][C:6]2[N:7]=[C:2]([NH:1][CH2:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]3)[N:3]=[CH:4][C:5]=2[CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5987Sulfamic AcidHCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 516892Sodium BicarbonateHCID 53281136-(2,6-Dichlorophenyl)pyrido[2,3-d]pyrimidine-2,7-diamine

Product 1

HCID 53281486-(2,6-dichlorophenyl)-2-N-[3-(4-methylpiperazin-1-yl)propyl]pyrido[2,3-d]pyrimidine-2,7-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine (3.0 g) from Example 1, sulfamic acid (1.9 g), and 1-(3-aminopropyl)-4-methylpiperazine (15 mL) was heated to approximately 150° C. for 24 hours. After cooling, the residue was dissolved in water. The aqueous solution was made alkaline with a solution of saturated sodium bicarbonate and extracted with dichloromethane several times. The dichloromethane layers were combined, dried over magnesium sulfate, and concentrated in vacuo. The residue was recrystallized from ethyl acetate to give 2.0 g of 6-(2,6-dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine, CIMS (1% NH3 in CH4): 474=M+ +C2H5, 446=M+ +H (Base); mp 208°-211° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane several times
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9674881c08004af9ba181216cc7781b2
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05733913

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes