Potassium Acetate → 2,6-Diethoxy-3'-fluoro-4'-morpholin-4-ylmethyl-biphenyl-4-ylmethy-pyrimidine-2,4-diamine

HRID 2416307Notes

Reaction equation

HRID 2416307 reaction equation
BrC1C=CC(CN2CC[O:10][CH2:9][CH2:8]2)=C(F)C=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.[C:34]([O-:37])(=O)[CH3:35].[K+].C(OC1C=C(C=C(OCC)C=1I)CC1C(N)=NC(N)=NC=1)C.C(O[C:64]1[CH:69]=[C:68]([CH2:70][C:71]2[C:72]([NH2:78])=[N:73][C:74]([NH2:77])=[N:75][CH:76]=2)[CH:67]=[C:66](OCC)[C:65]=1[C:82]1[CH:87]=[CH:86][C:85]([CH2:88][N:89]2[CH2:94][CH2:93][O:92][CH2:91][CH2:90]2)=[C:84]([F:95])[CH:83]=1)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:9]([O:10][C:74]1([NH2:77])[N:73]=[C:72]([NH2:78])[C:71]([CH2:70][C:68]2[CH:69]=[CH:64][C:65]([C:82]3[CH:87]=[CH:86][C:85]([CH2:88][N:89]4[CH2:94][CH2:93][O:92][CH2:91][CH2:90]4)=[C:84]([F:95])[CH:83]=3)=[CH:66][CH:67]=2)=[C:76]([O:37][CH2:34][CH3:35])[NH:75]1)[CH3:8]

Participants

7

Reactant 5

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 219145034-(4-Bromo-2-fluorobenzyl)morpholineHCID 226369195-(3,5-Diethoxy-4-iodo-benzyl)-pyrimidine-2,4-diamineHCID 226369605-(2,6-Diethoxy-3'-fluoro-4'-morpholin-4-ylmethyl-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine

Product 1

HCID 1363883892,6-Diethoxy-3'-fluoro-4'-morpholin-4-ylmethyl-biphenyl-4-ylmethy-pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

Analogously to example (4a), starting from 4-(4-bromo-2-fluoro-benzyl)-morpholine (274 mg; 1 mmol), bis(pinacolato)diboron (380 mg; 1.5 mmol), potassium acetate (294 mg; 3 mmol), bis(triphenylphosphine)palladium(II) dichloride (47 mg; 0.07 mmol) and from 5-(3,5-diethoxy-4-iodo-benzyl)-pyrimidine-2,4-diamine (example 1) (248 mg; 0.6 mmol), 166 mg (34%) 5-(2,6-diethoxy-3′-fluoro-4′-morpholin-4-ylmethyl-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine are obtained as a pale yellow powder.

Workup

  1. customare obtained as a pale yellow powder

Sources & evidence

ORD record
ord-258c51d9e3ad4e469eb720c55ba17d25
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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