(R)-tert-Butyl 4-fluoro-2-(4-(8-fluorochroman-4-ylamino)-5-nitropyrimidin-2-ylamino)phenylcarbamate → (R)-N2-(2-amino-5-fluorophenyl)-N4-(8-fluorochroman-4-yl)-5-nitropyrimidine-2,4-diamine

HRID 1363185Notes

Reaction equation

HRID 1363185 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)OC(C)(C)C)=[C:4]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C@H:24]3[C:33]4[C:28](=[C:29]([F:34])[CH:30]=[CH:31][CH:32]=4)[O:27][CH2:26][CH2:25]3)[C:20]([N+:35]([O-:37])=[O:36])=[CH:19][N:18]=2)[CH:3]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[NH:16][C:17]1[N:22]=[C:21]([NH:23][C@H:24]2[C:33]3[C:28](=[C:29]([F:34])[CH:30]=[CH:31][CH:32]=3)[O:27][CH2:26][CH2:25]2)[C:20]([N+:35]([O-:37])=[O:36])=[CH:19][N:18]=1

Participants

3

Reactant 1

HCID 66970500(R)-tert-Butyl 4-fluoro-2-(4-(8-fluorochroman-4-ylamino)-5-nitropyrimidin-2-ylamino)phenylcarbamate

Product 1

HCID 66970617(R)-N2-(2-amino-5-fluorophenyl)-N4-(8-fluorochroman-4-yl)-5-nitropyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A freshly prepared solution of 30% TFA/DCM (100 mL) was added to (R)-tert-butyl 4-fluoro-2-(4-(8-fluorochroman-4-ylamino)-5-nitropyrimidin-2-ylamino)phenylcarbamate and the solution was stirred at room temperature for 60 min. The solvents were removed in vacuo to yield (R)—N2-(2-amino-5-fluorophenyl)-N4-(8-fluorochroman-4-yl)-5-nitropyrimidine-2,4-diamine that was carried on without further purification. MH+=415.

Workup

  1. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-e2fbb5d932234da690a0fb83edf1e1df
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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