Dichloromethane → 1-(6-(4-Aminonaphthalen-1-yloxy)pyrimidin-4-yl)urea

HRID 2069157Notes

Reaction equation

HRID 2069157 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]([NH2:24])=[O:23])[CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.C(Cl)Cl.C1COCC1.[H][H]>CO.CC(O)=O.[Pt]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]([NH2:24])=[O:23])[CH:16]=2)=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 674217171-(6-(4-Nitronaphthalen-1-yloxy)pyrimidin-4-yl)ureaHCID 178418361HCID 178418361, compound

Product 1

HCID 674237641-(6-(4-Aminonaphthalen-1-yloxy)pyrimidin-4-yl)urea

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(6-(4-nitronaphthalen-1-yloxy)pyrimidin-4-yl)urea (60 mg, 0.184 mmol) in a mixture of MeOH, DCM and THF (1:1:1 v/v/v, 30 mL) containing AcOH (2 drops) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, RT, 70 mm CatCart, 10% Pt/C, full hydrogen mode). The resulting solution was evaporated in vacuo to afford the title compound, Intermediate R1, as a brown glassy solid (58 mg, 76% purity, 81%); Rt 1.23 min (Method 1 basic); m/z 296 (M+H)+ (ES+). This material was used directly in the next step (below) without further purification.

Workup

  1. customThe resulting solution was evaporated in vacuo

Sources & evidence

ORD record
ord-0ab5e961848544bc86a4368208a1f02a
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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