Triethylamine → HCID 178433333, compound

HRID 641681Notes

Reaction equation

HRID 641681 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[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]([OH:20])[CH2:16][CH2:15]3)[C:6]=2[N:7]=1.[B-](F)(F)(F)[C:23]1[NH:27][N:26]=[CH:25][CH:24]=1.[K+].C(N(CC)CC)C>C(O)C>[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[C:5]2[CH:11]=[C:10]([C:25]3[CH:24]=[CH:23][NH:27][N:26]=3)[C:9](=[O:13])[N:8]([C@H:14]3[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 25212877Potassium trifluoro(1H-pyrazol-5-yl)borate(1-)HCID 178433331HCID 178433331, compound

Product 1

HCID 178433333HCID 178433333, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-amino-6-bromo-8-((trans)-4-hydroxycyclohexyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (100 mg, 0.283 mmol), potassium 1H-pyrazole-5-trifluoroborate (98.5 mg, 0.566 mmol), and triethylamine (197 uL, 1.42 mmol) in ethanol (3.0 mL) was bubbled with argon. PdCl2(dppf)1:1 w/CH2Cl2 was added, the vial was sealed and the mixture was bubbled with argon again, then heated in the microwave for 30 minutes at 100° C., then 60 minutes at 150° C. The reaction mixture was concentrated and purified by flash chromatography eluting with 1:1 ethyl acetate:chloroform/7 N ammonia in methanol (0.5-7%). The fractions containing the desired product were combined and concentrated and the solids were recrystallized from methanol/chloroform to afford 2-amino-8-((trans)-4-hydroxycyclohexyl)-4-methyl-6-(1H-pyrazol-3-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (32 mg, 33%).

Workup

  1. customwas bubbled with argon
  2. additionPdCl2(dppf)1:1 w/CH2Cl2 was added
  3. customthe vial was sealed
  4. customthe mixture was bubbled with argon again
  5. custom60 minutes
  6. customat 150° C
  7. concentrationThe reaction mixture was concentrated
  8. custompurified by flash chromatography
  9. washeluting with 1:1 ethyl acetate
  10. additionThe fractions containing the desired product
  11. concentrationconcentrated
  12. customthe solids were recrystallized from methanol/chloroform

Sources & evidence

ORD record
ord-5a3d08dc697545419793165b7f35ecd9
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

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