Morpholine → HCID 59299558, compound

HRID 2386606Notes

Reaction equation

HRID 2386606 reaction equation
[Cl:1][C:2]1[N:10](CC=C)[C:9]2[C:8](=[O:14])[N:7]([CH2:15][CH2:16][CH2:17][C:18]([F:21])([F:20])[F:19])[C:6](=[O:22])[N:5]([CH2:23][CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27])[C:4]=2[N:3]=1.N1CCOCC1>O1CCCC1.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>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:14])[N:7]([CH2:15][CH2:16][CH2:17][C:18]([F:20])([F:21])[F:19])[C:6](=[O:22])[N:5]([CH2:23][CH2:24][CH2:25][C:26]([F:29])([F:27])[F:28])[C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 59299579HCID 59299579, compound

Product 1

HCID 59299558HCID 59299558, compoundYield 16.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

8-chloro-7-(2-propen-1-yl)-1,3-bis(4,4,4-trifluorobutyl)-3,7-dihydro-1H-purine-2,6-dione (478 mg, 1.1 mmol) and morpholine (937 ul, 11 mmol) were degassed with nitrogen in tetrahydrofuran (10 ml) and then tetrakis(triphenylphosphine)palladium(0) (123 mg, 0.11 mmol) was added and the reaction stirred at room temperature overnight. The reaction mixture was partitioned between dichloromethane and hydrochloric acid 2N. The organic phase was separated and reduced to give the crude product. This was purified by aminopropyl SPE (5 g) followed by re-crystallisation from acetonitrile to afford the title compound (75.5 mg, 16.9%). NMR. δH (400 MHz, CDCl3) 1.96-2.13 (m, 4H), 2.15-2.29 (m, 4H), 4.15-4.23 (m, 4H), 12.94 (br. s, 1H); m/z 407 [MH+].

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and hydrochloric acid 2N
  2. customThe organic phase was separated
  3. customto give the crude product
  4. customThis was purified by aminopropyl SPE (5 g)
  5. customfollowed by re-crystallisation from acetonitrile

Sources & evidence

ORD record
ord-1a96b95172864b59a87d9d8cee2cb6b6
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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