Water → HCID 86710181, compound

HRID 2284415Notes

Reaction equation

HRID 2284415 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:5]2[N:11]=[CH:10][C:9]([C:12]3[O:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:13]=3)=[CH:8][C:6]=2[N:7]=1.B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C[N:39]([CH:41]=[O:42])[CH3:40].[OH2:43]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:9]([O:43][C:41]([NH:39][C:40]1[N:7]=[CH:6][C:5]([C:2]2[N:3]=[C:4]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:5]3[N:11]=[CH:10][C:9]([C:12]4[O:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:13]=4)=[CH:8][C:6]=3[N:7]=2)=[CH:4][N:3]=1)=[O:42])([CH3:12])([CH3:10])[CH3:8]

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 61668Boronic AcidHCID 62657Potassium Phosphate, TribasicHCID 86710180HCID 86710180, compound

Product 1

HCID 86710181HCID 86710181, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
95 °C

Procedure

To a 50 mL sealed tube, methyl 5-(2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-7-yl)furan-2-carboxylate (0.35 g, 0.0009 mol), (2-(tert-butoxycarbonyl)amino)pyrimidin-5-yl)boronic acid (0.33 g, 0.0014 mol), potassium phosphate (0.39 g, 0.0018 mol), DMF (15 mL) and water (5 mL) were added. The reaction mixture was degassed with N2 for 5-10 minutes. To the same reaction mixture, Pd(PPh3)4 (0.053 g, 0.000046 mol) was added and the mixture was degassed again with N2 for 5-10 minutes. The reaction mixture was stirred at 95° C. for 1 hour. The reaction mixture was cooled and mixed with water. A precipitate formed which was collected by filtration. The filtered solid was purified by flash column chromatography (3% methanol in chloroform) to provide methyl 5-(2-(2-((tert-butoxycarbonyl)amino)pyrimidin-5-yl)-4-morpholinopyrido[3,2-d]pyrimidin-7-yl)furan-2-carboxylate (0.3 g). LC-MS (ESI): Calculated mass: 533.0; Observed mass: 434.1 [M-Boc+H]+ (RT=1.60 min).

Workup

  1. customTo a 50 mL sealed tube
  2. customThe reaction mixture was degassed with N2 for 5-10 minutes
  3. customthe mixture was degassed again with N2 for 5-10 minutes
  4. temperatureThe reaction mixture was cooled
  5. additionmixed with water
  6. customA precipitate formed which
  7. filtrationwas collected by filtration
  8. customThe filtered solid was purified by flash column chromatography (3% methanol in chloroform)

Sources & evidence

ORD record
ord-6180a9b649c544518e0190c335dd2bc0
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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