3-Bromo-2-methyl-1-propene → HCID 66613616, compound

HRID 510085Notes

Reaction equation

HRID 510085 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:28])[NH:6]2.CCN(P1(N(C)CCCN1C)=N[C:36]([CH3:39])([CH3:38])[CH3:37])CC.BrCC(C)=C>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:28])[N:6]2[CH2:38][C:36]([CH3:39])=[CH2:37]

Participants

5

Reactant 3

HCID 3577853-Bromo-2-methyl-1-propeneHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 666136276-amino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)- 7,9-dihydro-8H-purin-8-one

Product 1

HCID 66613616HCID 66613616, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

200 mg (0.531 mmol) of the compound from example 33 and 145 mg (0.531 mmol) of BEMP were initially charged in 10 ml of dimethylformamide, and a solution of 72 mg (0.531 mmol) of 3-bromo-2-methylprop-1-ene 2 ml of dimethylformamide was added dropwise at 0° C. within 10 min. The mixture was stirred at 0° C. for 1 h. Subsequently, the reaction solution was concentrated under reduced pressure and the residue was purified by means of preparative HPLC (eluent: acetonitrile/water, gradient 10:90→90:10). 88 mg of the title compound were obtained (37% of theory).

Workup

  1. concentrationSubsequently, the reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by means of preparative HPLC (eluent: acetonitrile/water, gradient 10:90→90:10)

Sources & evidence

ORD record
ord-7bbd9ad0e2704b2eb3495de7c46c1ca2
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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