Potassium Carbonate → 3-(4-Aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzaldehyde
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH2:18])[C:16]=3[N:17]=2)[CH:5]=[CH:6][CH:7]=1.FC1C=C(B(O)O)C=C([CH:26]=[O:27])C=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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>[NH2:18][C:15]1[C:16]2[N:17]=[C:8]([C:4]3[CH:5]=[C:6]([CH:7]=[C:2]([F:1])[CH:3]=3)[CH:26]=[O:27])[CH:9]=[CH:10][C:11]=2[N:12]=[CH:13][N:14]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
A suspension of 6-chloropyrido[3,2-d]pyrimidin-4-amine (1) (3.61 g, 20 mmol), 3-fluoro-5-formylphenylboronic acid (CAS 328956-60-1) (4.03 g, 24 mmol, 1.2 eq), Pd(PPh3)4 (1.16 g, 1.0 mmol, 0.05 eq), and K2CO3 (5.53 g, 40 mmol, 2.0 eq) in a mixture of dioxane (100 mL) and H2O (10 mL) was heated at 100° C. for 3 h. After it was cooled to r.t., the reaction was extracted with EtOAc (100 mL) and water (60 mL). The organic layer were washed with water and concentrated. The yellow solid was recrystallized in MeCN to give the titled product (4.8 g, yield: 90%).
Workup
- temperatureAfter it was cooled to r.t.
- extractionthe reaction was extracted with EtOAc (100 mL) and water (60 mL)
- washThe organic layer were washed with water
- concentrationconcentrated
- customThe yellow solid was recrystallized in MeCN
Sources & evidence
- ORD record
- ord-14d458fa545b4fc5a9defba99da2bef3
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382241B2
Reaction notes
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