Benzene → 4-Amino-6-benzyloxy-5-nitropyrimidine

HRID 619216Notes

Reaction equation

HRID 619216 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[Na].C1C=CC=CC=1.[CH2:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 244Benzyl AlcoholHCID 1012294-Pyrimidinamine, 6-chloro-5-nitro-HCID 5360545Sodium

Product 1

HCID 101059474-Amino-6-benzyloxy-5-nitropyrimidine

Conditions

Temperature
130 °C

Procedure

4-Amino-6-chloro-5-nitropyrimidine (Boon et al., J. Chem. Soc., 96-102 (1951)) (1.5 g, 8.6 mmol) was added to a solution of sodium (0.23 g, 9.9 mmol) in benzyl alcohol (14 mL). The solution was heated in a 130° C. oil bath for 3.5 h, and was poured into benzene (50 mL). A yellow solid was collected by filtration and washed with benzene. Crystallization from benzene/ether afforded an analytically pure sample of 3a: yield, 0.71 g (34%); mp 149-150° C.; UV (pH 1) lmax 284 nm (e=0.368×104), 333 (0.488×104); (pH 6.9) 284 (0.329×104), 336 (0.470×104); (pH 13) 290 (0.344×104), 333 (0.494×104); 1H NMR d 5.50 (s, 2 H, ArCH2), 7.33-7.49 (m, 5 H, ArH), 8.12-8.24 (br d, 2 H, NHa and NHb, exchange with D2O), 8.24 (s, 1 H, H-2); MS (EI) calcd. m/z for C11H10N4O3 246.0752, found 246.0751; Anal. (C11H10N4O3) C, H, N.

Workup

  1. filtrationA yellow solid was collected by filtration
  2. washwashed with benzene
  3. customCrystallization from benzene/ether

Sources & evidence

ORD record
ord-24a56484e1f544b5a311f76c23dd1804
Source dataset
uspto-grants-1999_09
Patent number
US05958932

Reaction notes

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