Trifluoroacetic acid → HCID 67415278, compound

HRID 1423009Notes

Reaction equation

HRID 1423009 reaction equation
BrCC1C=CC(C2CCCN2C(OC(C)(C)C)=O)=CC=1.ClCC1C=CC(C2C=CC=CN=2)=CC=1.[Cl:35][C:36]1[N:37]([CH2:52][C:53]2[CH:58]=[CH:57][C:56]([CH:59]3[CH2:63][CH2:62][CH2:61][N:60]3C(OC(C)(C)C)=O)=[CH:55][CH:54]=2)[CH:38]=[C:39]2[C:44]=1[C:43](=[O:45])[N:42]([CH3:46])[C:41](=[O:47])[N:40]2[CH2:48][CH:49]([CH3:51])[CH3:50].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:35][C:36]1[N:37]([CH2:52][C:53]2[CH:54]=[CH:55][C:56]([CH:59]3[CH2:63][CH2:62][CH2:61][NH:60]3)=[CH:57][CH:58]=2)[CH:38]=[C:39]2[C:44]=1[C:43](=[O:45])[N:42]([CH3:46])[C:41](=[O:47])[N:40]2[CH2:48][CH:49]([CH3:51])[CH3:50]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 219897292-(4-(Chloromethyl)phenyl)pyridineHCID 67402296HCID 67402296, compoundHCID 67413628HCID 67413628, compound

Product 1

HCID 67415278HCID 67415278, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The synthetic procedure of this compound is analogous to EXAMPLE 6 wherein tert-butyl 2-(4-(bromomethyl)phenyl)pyrrolidine-1-carboxylate is used in step 2 instead of 2-(4-(chloromethyl)phenyl)pyridine. The obtained tert-butyl 2-(4-((5-chloro-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrrolo[3,4-d]pyrimidin-6-yl)methyl)phenyl)pyrrolidine-1-carboxylate is deprotected with TFA in CH2Cl2 at room temperature to give 5-chloro-1-isobutyl-3-methyl-6-(4-(pyrrolidin-2-yl)benzyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione, which is N-methylated with 37% formaldehyde aqueous solution and sodium borohydride in methanol at room temperature to give 5-chloro-1-isobutyl-3-methyl-6-(4-(1-methylpyrrolidin-2-yl)benzyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione in a good overall yield. The obtained intermediate reacts with aniline using the procedure described in step 3 of EXAMPLE 6 to give pure product after HPLC purification. MS (ESI) m/z 486.3 [M+H]+.

Sources & evidence

ORD record
ord-b66b3a6cc0eb45b78f690d478d3f2d51
Source dataset
uspto-grants-2015_01
Patent number
US08927556B2

Reaction notes

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