Carbon tetrabromide → N,N-Di-Boc-5-(bromomethyl)pyrimidin-2-amine

HRID 1789867Notes

Reaction equation

HRID 1789867 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[C:25]([O:29][C:30]([N:32]([C:40]1[N:45]=[CH:44][C:43](CO)=[CH:42][N:41]=1)[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:31])([CH3:28])([CH3:27])[CH3:26]>ClCCl>[Br:24][CH2:20][C:43]1[CH:42]=[N:41][C:40]([N:32]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])=[N:45][CH:44]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 220360932-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-pyrimidin

Product 1

HCID 22036062N,N-Di-Boc-5-(bromomethyl)pyrimidin-2-amineYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine (2.71 g, 10.73 mmol) and CBr4 (4.89 g, 14.8 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-pyrimidin (3.20 g, 9.83 mmol) in dichloromethane (30 mL) at 0° C. The reaction mixture was stirred for 1 h and was then diluted with dichloromethane. The organic phase was washed with water, dried and concentrated under reduced pressure. Flash chromatography (CH2Cl2) gave 5-bromomethyl-2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin (2.55 g, 67%).

Workup

  1. washThe organic phase was washed with water
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b1f95d04a7e45cc9e1fbc6ff7510f68
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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