(R)-N2-(2-(2,4-Dimethoxybenzylamino)-4-fluorophenyl)-N4-(8-fluorochroman-4-yl)-5-nitropyrimidine-2,4-diamine → (R)-N2-(2-(2,4-dimethoxybenzylamino)-4-fluorophenyl)-N4-(8-fluorochroman-4-yl)pyrimidine-2,4,5-triamine

HRID 1363181Notes

Reaction equation

HRID 1363181 reaction equation
[CH3:1][O:2][C:3]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:4]=1[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[NH:14][C:15]1[N:20]=[C:19]([NH:21][C@H:22]2[C:31]3[C:26](=[C:27]([F:32])[CH:28]=[CH:29][CH:30]=3)[O:25][CH2:24][CH2:23]2)[C:18]([N+:33]([O-])=O)=[CH:17][N:16]=1>O.C1COCC1.[Ni]>[CH3:1][O:2][C:3]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:4]=1[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[NH:14][C:15]1[N:20]=[C:19]([NH:21][C@H:22]2[C:31]3[C:26](=[C:27]([F:32])[CH:28]=[CH:29][CH:30]=3)[O:25][CH2:24][CH2:23]2)[C:18]([NH2:33])=[CH:17][N:16]=1

Participants

5

Reactant 1

HCID 69105486(R)-N2-(2-(2,4-Dimethoxybenzylamino)-4-fluorophenyl)-N4-(8-fluorochroman-4-yl)-5-nitropyrimidine-2,4-diamine

Product 1

HCID 69105872(R)-N2-(2-(2,4-dimethoxybenzylamino)-4-fluorophenyl)-N4-(8-fluorochroman-4-yl)pyrimidine-2,4,5-triamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an Ar atmosphere, a catalytic amount of a Raney Ni solution in water was added to a solution of (R)—N2-(2-(2,4-dimethoxybenzylamino)-4-fluorophenyl)-N4-(8-fluorochroman-4-yl)-5-nitropyrimidine-2,4-diamine (21 mg) in THF. The flask was closed with a septum, evacuated under house vacuum and hydrogen added via balloon. The resulting suspension was stirred at RT for 2 hr, when the H2 balloon was removed, the mixture evacuated and filtered through a plug of celite, that was thoroughly rinsed with THF and MeOH, to yield (R)—N2-(2-(2,4-dimethoxybenzylamino)-4-fluorophenyl)-N4-(8-fluorochroman-4-yl)pyrimidine-2,4,5-triamine that was used directly.

Workup

  1. customThe flask was closed with a septum
  2. customevacuated under house vacuum and hydrogen
  3. additionadded via balloon
  4. customwhen the H2 balloon was removed
  5. customthe mixture evacuated
  6. filtrationfiltered through a plug of celite, that
  7. washwas thoroughly rinsed with THF and MeOH

Sources & evidence

ORD record
ord-f8655063e0ea40d187f67fcdaec3c850
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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