Acetic Acid → N-(6-(4-Aminonaphthalen-1-yloxy)pyrimidin-4-yl)-2-methoxy acetamid

HRID 2069144Notes

Reaction equation

HRID 2069144 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([N+:24]([O-])=O)=[CH:16][CH:15]=2)[N:10]=[CH:9][N:8]=1)=[O:5].CC(O)=O.[H][H]>CO.C(Cl)Cl.[Pt]>[NH2:24][C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([O:13][C:11]2[N:10]=[CH:9][N:8]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][O:2][CH3:1])[CH:12]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 708814402-Methoxy-N-(6-(4-nitronaphthalen-1-yloxy)pyrimidin-4-yl)acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 68229622N-(6-(4-Aminonaphthalen-1-yloxy)pyrimidin-4-yl)-2-methoxy acetamid

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methoxy-N-(6-(4-nitronaphthalen-1-yloxy)pyrimidin-4-yl)acetamide (400 mg, 1.13 mmol) in a mixture of MeOH and DCM and AcOH (2:2:1 v/v/v, 15 mL) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, RT, 55 mm CatCart, 10% Pt/C, full hydrogen mode) and was then evaporated in vacuo to afford the title compound, Intermediate M1, as a brown oil (400 mg, 90% purity, 98%); Rt 3.57 min (Method 1 basic); m/z 325 (M+H)+ (ES+).

Workup

  1. customwas then evaporated in vacuo

Sources & evidence

ORD record
ord-ab46738158844652b3d8a7665256c5c2
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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