Dichloromethane → HCID 178488428, compound

HRID 472232Notes

Reaction equation

HRID 472232 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:22])[C:5]2[CH:11]=[C:10](Br)[C:9](=[O:13])[N:8]([C@H:14]3[CH2:19][CH2:18][C@H:17]([O:20][CH3:21])[CH2:16][CH2:15]3)[C:6]=2[N:7]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][N:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>O.C(COC)OC>[NH2:1][C:2]1[N:3]=[C:4]([CH3:22])[C:5]2[CH:11]=[C:10]([C:28]3[CH:27]=[N:26][C:25]([O:24][CH3:23])=[CH:30][CH:29]=3)[C:9](=[O:13])[N:8]([C@H:14]3[CH2:19][CH2:18][C@H:17]([O:20][CH3:21])[CH2:16][CH2:15]3)[C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 178496588HCID 178496588, compound

Product 1

HCID 178488428HCID 178488428, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a vial containing 2-amino-6-bromo-8-(trans-4-methoxycyclohexyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (75 mg, 0.20 mmol), 2-methoxy-5-pyridineboronic acid (37.5 mg, 0.245 mmol) and cesium carbonate was added PdCl2(dppf)1:1 w/CH2Cl2 followed by 5:1 dimethoxyethane:water (3 mL, degassed by bubbling with argon). The vial was capped and heated in the microwave for 30 minutes at 100° C. The reaction mixture was concentrated and the crude product was purified by flash chromatography eluting with chloroform/methanol (0-5%). The fractions containing the desired product were concentrated and the solids were triturated with methyltertbutyl ether to afford 2-amino-8-(trans-4-methoxycyclohexyl)-6-(6-methoxypyridin-3-yl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (33 mg, 40%).

Workup

  1. customThe vial was capped
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude product was purified by flash chromatography
  4. washeluting with chloroform/methanol (0-5%)
  5. additionThe fractions containing the desired product
  6. concentrationwere concentrated
  7. customthe solids were triturated with methyltertbutyl ether

Sources & evidence

ORD record
ord-9381a207fb0f4326b356971a4c205824
Source dataset
uspto-grants-2014_01
Patent number
US08633204B2

Reaction notes

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