Triphenylphosphine → HCID 58416768, compound

HRID 872417Notes

Reaction equation

HRID 872417 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:15][C:16]1[N:21]=[C:20]([CH2:22]O)[CH:19]=[CH:18][N:17]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:22][C:20]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:15])[N:21]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2004934-Pyrimidinemethanol, 2-amino-HCID 3438294-Nitro-1-naphtholHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 58416768HCID 58416768, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

A mixture of 4-nitronaphthol (741 mg, 3.92 mmol), (2-aminopyrimidin-4-yl)methanol (31) (700 mg, 3.92 mmol) and PPh3 (1233 mg, 4.70 mmol) in THF (20 mL) was cooled to −50° C. under nitrogen and was treated dropwise over 5 min with DIAD (996 μl, 4.70 mmol). After completion of the addition, the mixture was allowed to warm to RT and stirred for 1 hr. A yellow precipitate forms during this time. After stirring overnight, the volatiles were evaporated and the residue triturated from MeOH (50 mL). The pale yellow solid collected by filtration and washed with diethyl ether (50 mL) to give 4-((4-nitronaphthalen-1-yloxy)methyl)pyrimidin-2-amine (32) (1.1 g, 93%): m/z 297 (M+H)+ (ES+).

Workup

  1. additionAfter completion of the addition
  2. temperatureto warm to RT
  3. stirringAfter stirring overnight
  4. customthe volatiles were evaporated
  5. customthe residue triturated from MeOH (50 mL)
  6. filtrationThe pale yellow solid collected by filtration
  7. washwashed with diethyl ether (50 mL)

Sources & evidence

ORD record
ord-49a69735e1b8454db95403bf1ea54b62
Source dataset
uspto-grants-2015_03
Patent number
US08975285B2

Reaction notes

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