Water → 4-Chloro-N-[5-(2,4-diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-butyramide

HRID 925172Notes

Reaction equation

HRID 925172 reaction equation
[NH2:1][C:2]1[C:3]([O:20][CH3:21])=[CH:4][C:5]([CH:17]([CH3:19])[CH3:18])=[C:6]([CH:16]=1)[O:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1.[Cl:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27].O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:22][CH2:23][CH2:24][CH2:25][C:26]([NH:1][C:2]1[CH:16]=[C:6]([O:7][C:8]2[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=2)[C:5]([CH:17]([CH3:19])[CH3:18])=[CH:4][C:3]=1[O:20][CH3:21])=[O:27]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 783704-Chlorobutyryl chlorideHCID 595985735-(5-Amino-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

Product 1

HCID 595985764-Chloro-N-[5-(2,4-diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-butyramideYield 91%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(5-amino-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (0.400 g, 1.4 mmol) in 15 ml CHCl3 and Na2HPO4 (0.392 g, 2.8 mmol) was added 4-chlorobutyryl chloride (0.194 g, 1.4 mmol) drop-wise. After 4.5 h, H2O and CH2Cl2 were added and the mixture was allowed to stir 15 min. The mixture was neutralized with 2N Na2CO3 and extracted with CH2Cl2. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 4-chloro-N-[5-(2,4-diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-butyramide (0.495 g, 91%) as brown foam; [MH]+=394.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4cbc209c45bc415dac04b11b2bf1368a
Source dataset
uspto-grants-2016_03
Patent number
US09284279B2

Reaction notes

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