1-Butanol → HCID 178450628, compound

HRID 472241Notes

Reaction equation

HRID 472241 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.CN([CH:25]=[O:26])C.[CH2:27]([OH:31])[CH2:28][CH2:29][CH3:30].C1CCN2C(=NCCC2)CC1>CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].[B-](F)(F)(F)F.CC([PH+](C(C)(C)C)C(C)(C)C)(C)C.O>[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[C:5]2[CH:11]=[C:10]([C:25]([O:31][CH2:27][CH2:28][CH2:29][CH3:30])=[O:26])[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

8

Reactant 4

HCID 2631-ButanolHCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178433331HCID 178433331, compound

Product 1

HCID 178450628HCID 178450628, compound

Reagents, catalysts & solvents 3

HCID 2734635Tri-tert-butylphosphine tetrafluoroborateCatalystHCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)CatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A microwave vial was charged with Mo(CO)6 (264 mg, 1.0 mmol), Herrmann's palladacycle (23 mg, 0.025 mmol), [(t-Bu)3PH]BF4 (15 mg, 0.050 mmol), 2-amino-6-bromo-8-(trans-4-hydroxycyclohexyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (353 mg, 1.0 mmol), DMF (5 mL) and butanol (5 mL). DBU (412 ml, 3.0 mmol) was added, followed by rapid sealing of the vial under air. The vial was then heated to 120° C. by microwave irradiation for 30 minutes. After cooling, the reaction mixture was slurried with water and filtered. The precipitate was washed with ether and dried to afford 253 mg of butyl 2-amino-8-(trans-4-hydroxycyclohexyl)-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. washThe precipitate was washed with ether
  4. customdried

Sources & evidence

ORD record
ord-f6dcea13bbc84484af4bf1be9cdd63d8
Source dataset
uspto-grants-2014_01
Patent number
US08633204B2

Reaction notes

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