tert-Butyl isocyanate → 3-Tert-butyl-1-[6-(2,6-dibromophenyl)-2-{[3-(diethylamino)propyl]amino}pyrido[2,3-d]pyrimidin-7-yl]urea

HRID 617956Notes

Reaction equation

HRID 617956 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[C:9]1[C:27]([NH2:28])=[N:26][C:12]2[N:13]=[C:14]([NH:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[N:15]=[CH:16][C:11]=2[CH:10]=1.[C:29]([N:33]=[C:34]=[O:35])([CH3:32])([CH3:31])[CH3:30]>>[C:29]([NH:33][C:34]([NH:28][C:27]1[C:9]([C:3]2[C:2]([Br:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Br:8])=[CH:10][C:11]2[CH:16]=[N:15][C:14]([NH:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])=[N:13][C:12]=2[N:26]=1)=[O:35])([CH3:32])([CH3:31])[CH3:30]

Participants

3

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 53281226-(2,6-dibromophenyl)-2-N-[3-(diethylamino)propyl]pyrido[2,3-d]pyrimidine-2,7-diamine

Product 1

HCID 53281233-Tert-butyl-1-[6-(2,6-dibromophenyl)-2-{[3-(diethylamino)propyl]amino}pyrido[2,3-d]pyrimidin-7-yl]ureaYield 52.9%

Procedure

6-(2,6-Dibromo-phenyl)-N2 -[3-diethylamino-propyl)-pyrido[2,3-d]pyrimidine-2,7-diamine (0.34 g) from Example 61 was reacted with 0.066 g of tert-butyl isocyanate according to the general procedure of Example 54. The crude residue was purified by thin layer chromatography with ethyl acetate:ethanol:triethylamine (9:2:1) followed by preparative HPLC chromatography using a Vydac 218 TP 1022 reverse phase column with a gradient elution of 0.1% trifluoroacetic acid/water and 0.1% trifluoroacetic acid/acetonitrile to give 0.214 g of the title compound, ESMS (20/80 MEOH/CH3CN+0.1% AcOH): 606=M+ +H; mp dec. >45° C.

Workup

  1. customThe crude residue was purified by thin layer chromatography with ethyl acetate:ethanol:triethylamine (9:2:1)
  2. washwith a gradient elution of 0.1% trifluoroacetic acid/water and 0.1% trifluoroacetic acid/acetonitrile

Sources & evidence

ORD record
ord-28e3fbda02464a669c2e1f1cf9c7f21e
Source dataset
uspto-grants-1999_09
Patent number
US05952342

Reaction notes

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