Water → tert-Butyl {3-[7-amino-6-carbamoyl-2-(4-morpholin-4-ylphenylamino)-5-oxo-5H-pyrido[2,3-d]pyrimidin-8-yl]propyl}carbamate

HRID 871863Notes

Reaction equation

HRID 871863 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[C:16]2[N:17]=[C:18](Cl)[N:19]=[CH:20][C:15]=2[C:14](=[O:22])[C:13]([C:23](=[O:25])[NH2:24])=[C:12]1[NH2:26])([CH3:4])([CH3:3])[CH3:2].[N:28]1([C:34]2[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.O.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[NH2:26][C:12]1[N:11]([CH2:10][CH2:9][CH2:8][NH:7][C:6](=[O:27])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:16]2[N:17]=[C:18]([NH:40][C:37]3[CH:36]=[CH:35][C:34]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:39][CH:38]=3)[N:19]=[CH:20][C:15]=2[C:14](=[O:22])[C:13]=1[C:23](=[O:25])[NH2:24]

Participants

6

Reactant 4

HCID 962WaterHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 516892Sodium BicarbonateHCID 86673138tert-Butyl [3-(7-amino-6-carbamoyl-2-chloro-5-oxo-5H-pyrido[2,3-d]pyrimidin-8-yl)propyl]carbamate

Product 1

HCID 67325689tert-Butyl {3-[7-amino-6-carbamoyl-2-(4-morpholin-4-ylphenylamino)-5-oxo-5H-pyrido[2,3-d]pyrimidin-8-yl]propyl}carbamateYield 20%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.60 g (1.51 mmol) of the product prepared in step 11.3 and 0.53 g (3.02 mmol) of 4-morpholin-4-ylphenylamine in 6.5 mL of NMP is placed in a 10 mL microwave tube. The sealed tube is placed in the microwave oven (CEM machine, Discovery model) and the mixture is heated under pressure at 120°C. for 60 minutes at a power of 75 W, and then cooled to room temperature. 15 mL of water and then 5 mL of saturated aqueous NaHCO3 are added and the precipitate formed is drained by suction and then dried in an oven. The crude solid is triturated in methanol, drained by suction and dried in an oven under vacuum. 0.159 g of the expected product is obtained in solid form. Yield=20%.

Workup

  1. customis placed in a 10 mL microwave tube
  2. temperaturecooled to room temperature
  3. customthe precipitate formed
  4. customdried in an oven
  5. customThe crude solid is triturated in methanol
  6. customdried in an oven under vacuum

Sources & evidence

ORD record
ord-ab8b98b3ed4a42bd93a1638d7a2007b1
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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