Potassium Carbonate → HCID 10292512, compound

HRID 2188247Notes

Reaction equation

HRID 2188247 reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]3[CH:29]=CC(C(OC)=O)=C[CH:21]=3)=[C:14]([F:30])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2].CC1(C)C(C)(C)OB(C2C=[N:41][C:42]([NH2:45])=[N:43]C=2)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.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>[NH2:45][C:42]1[N:43]=[CH:21][C:20]([C:19]#[C:18][C:15]2[CH:16]=[CH:17][C:12]([N:8]3[CH2:7][C@H:6]([CH2:5][NH:4][C:1](=[O:3])[CH3:2])[O:10][C:9]3=[O:11])=[CH:13][C:14]=2[F:30])=[CH:29][N:41]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 9844427HCID 9844427, compoundHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol ester

Product 1

HCID 10292512HCID 10292512, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of Example 1F (41 mg) in degassed DME (1.3 mL) was treated with 5-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)-pyrimidin-2-ylamine (41.5mg, prepared according to the procedure described in Tetrahedron Letters, 1997, 38, 3447-3450), tetrakis(triphenylphosphine)palladium (12 mg) and a degassed 2 N solution of potassium carbonate in water (0.2 mL). The tube was sealed, heated to 70° C., and stirred for 20 hours. The reaction mixture was then cooled to room temperature, concentrated, and diluted with dichloromethane (4 mL). The precipitate was removed by filtration and washed with water (10 mL) and then cold acetone (3 mL) to provide the desired product. MS (ESI(+)) m/e 370 (M+H)+; 1H NMR (300 MHz, MeOH) δ 8.49 (s, 2H), 7.61 (dd, J=2.1, 12 Hz, 1H), 7.57 (t, J=8.4 Hz, 1H), 7.32 (dd, J=2.1, 8.7 Hz, 1H), 4.8 (m, 1H), 4.16 (t, J=9 Hz, 1H), 3.83 (dd, J=6.3, 9.6 Hz, 1H), 3.56(d, J=5.4 Hz, 2H), 1.96 (s, 3H).

Workup

  1. customprepared
  2. customThe tube was sealed
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. concentrationconcentrated
  5. additiondiluted with dichloromethane (4 mL)
  6. customThe precipitate was removed by filtration
  7. washwashed with water (10 mL)

Sources & evidence

ORD record
ord-67159900b10d4d038244db7909f1c023
Source dataset
uspto-grants-2002_06
Patent number
US06410728B1

Reaction notes

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