HCID 59726886, compound → HCID 59727003, compound

HRID 1363139Notes

Reaction equation

HRID 1363139 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:4]=1[CH2:5][NH:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=2[F:22])[C:10]([N+:23]([O-])=O)=[CH:9][N:8]=1>C1COCC1.[Ni]>[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:4]=1[CH2:5][NH:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]2[C:16]([F:22])=[CH:17][CH:18]=[CH:19][C:20]=2[F:21])[C:10]([NH2:23])=[CH:9][N:8]=1

Participants

4

Reactant 1

HCID 59726886HCID 59726886, compound

Product 1

HCID 59727003HCID 59727003, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Raney Ni was added to a solution of N2-(2,4-dimethoxybenzyl)-N4-(2,6-difluorobenzyl)-5-nitropyrimidine-2,4-diamine (0.80 g) in THF (50 mL) under argon flush. The suspension was evacuated, charged with hydrogen (balloon) and stirred for 16 hr. The resulting mixture was filtered through a celite plug that was thoroughly rinsed with THF and MeOH to yield N2-(2,4-dimethoxybenzyl)-N4-(2,6-difluorobenzyl)pyrimidine-2,4,5-triamine (54) that was used as such in the next reaction.

Workup

  1. customflush
  2. customThe suspension was evacuated
  3. additioncharged with hydrogen (balloon)
  4. filtrationThe resulting mixture was filtered through a celite plug that
  5. washwas thoroughly rinsed with THF and MeOH

Sources & evidence

ORD record
ord-bfd0fe0efa9d4e1188ef15dc9eebbcb4
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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