Sulfamic Acid → Ammonia

HRID 3445

Reaction equation

HRID 3445 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)[NH2:22].[CH2:26]([N:28]([CH2:31][CH2:32]N)[CH2:29][CH3:30])[CH3:27]>>[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][CH2:26][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[N:3]=[CH:4][C:5]=2[CH:11]=1.[NH3:22]

Participants

5

Reactant 3

HCID 5987Sulfamic AcidHCID 60993N,N-DiethylethylenediamineHCID 53281136-(2,6-Dichlorophenyl)pyrido[2,3-d]pyrimidine-2,7-diamine

Product 2

HCID 222AmmoniaYield 1%HCID 53281286-Arylpyrido[2,3-d]pyrimidine deriv. 26

Conditions

Temperature
150 °C

Procedure

A mixture of 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine (4.0 g) from Example 1, sulfamic acid (2.53 g), and diethylaminoethylamine (40 mL) was heated to approximately 150° C. for 20 hours. The excess diethylaminoethylamine was removed in vacuo. The resulting oil was dissolved in diethyl ether, diluted with hexane, and then filtered. The resulting solid was dissolved in dichloromethane which was washed several times with water, dried with magnesium sulfate, and concentrated in vacuo. The residue was crystallized from ethyl acetate to give the title compound 6-(2,6-dichlorophenyl)-N2 -(2-diethylamino-ethyl)-pyrido[2,3-d]pyrimidine-2,7-diamine, CIMS (1% NH3 in CH4): 433=M+ +C2H5, 405=M+ +H, 389=M+ -Et, 360; mp 216°-219.5° C.

Workup

  1. customThe excess diethylaminoethylamine was removed in vacuo
  2. dissolutionThe resulting oil was dissolved in diethyl ether
  3. additiondiluted with hexane
  4. filtrationfiltered
  5. dissolutionThe resulting solid was dissolved in dichloromethane which
  6. washwas washed several times with water
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-6a90e5dbf8d9440f860586cc73a69716
Source dataset
uspto-grants-1998_03
Patent number
US05733913

Linked notes

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