(2,4-Dimethoxypyrimidin-5-yl)boronic acid → HCID 86703224, compound

HRID 2204410Notes

Reaction equation

HRID 2204410 reaction equation
Br[C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]2[CH:10]([C:31]3[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[C:33]([F:39])[CH:32]=3)[N:11]([C:14]3[C:15](=[O:30])[N:16](CC4C=CC(OC)=CC=4)[CH:17]=[C:18]([Cl:20])[CH:19]=3)[C:12](=[O:13])[C:4]=2[CH:3]=1.[CH3:40][O:41][C:42]1[N:47]=[C:46]([O:48][CH3:49])[C:45](B(O)O)=[CH:44][N:43]=1.BrC1N(C(C)C)C2C(C3C=CC(C#N)=CC=3)N(C3C(=O)N(CC4C=CC(OC)=CC=4)C=C(Cl)C=3)C(=O)C=2C=1.COC1C(B2OC(C)(C)C(C)(C)O2)=CN=C(N)N=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[Cl:20][C:18]1[CH:19]=[C:14]([N:11]2[C:12](=[O:13])[C:4]3[CH:3]=[C:2]([C:45]4[C:46]([O:48][CH3:49])=[N:47][C:42]([O:41][CH3:40])=[N:43][CH:44]=4)[N:6]([CH:7]([CH3:8])[CH3:9])[C:5]=3[CH:10]2[C:31]2[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[C:33]([F:39])[CH:32]=2)[C:15](=[O:30])[NH:16][CH:17]=1

Participants

7

Reactant 4

HCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 591984044-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amineHCID 86703225HCID 86703225, compoundHCID 86703226HCID 86703226, compound

Product 1

HCID 86703224HCID 86703224, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in analogy to the procedure described for Example 125 but in the step corresponding to Step 125.1, 4-{2-bromo-5-[5-chloro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-pyridin-3-yl]-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-6-yl}-2-fluoro-benzonitrile (Intermediate BE) and 2,4-dimethoxypyrimidine-5-boronic acid were used instead of 4-{2-bromo-5-[5-chloro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-pyridin-3-yl]-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-6-yl}-benzonitrile and 4-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-ylamine respectively. Moreover, in this step, Pd(PPh3)4 was used instead of PdCl2(dppf).CH2Cl2 adduct. The title compound was obtained as a white solid. tR: 5.84 min (H PLC 2); ESI-MS: tR=0.94 min, [M+H]+ 549/551 (LC-MS 1); TLC: Rf=0.19 (EtOAc).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-2ce53208cbf9415fa1817ed267006395
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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