Formaldehyde → HCID 57905695, compound

HRID 1012994Notes

Reaction equation

HRID 1012994 reaction equation
[CH2:1]([N:8]([CH3:33])[CH:9]1[CH2:15][N:14]([C:16](OC(C)(C)C)=O)[CH2:13][CH2:12][N:11]2[C:23](=[O:32])[C:24]([OH:31])=[C:25]([C:27]([O:29][CH3:30])=[O:28])[N:26]=[C:10]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.C(N(CC)CC)C.[BH3-]C#N.[Na+]>C(Cl)Cl.C(O)(C(F)(F)F)=O.C(O)(=O)C>[CH2:1]([N:8]([CH3:33])[CH:9]1[CH2:15][N:14]([CH3:16])[CH2:13][CH2:12][N:11]2[C:23](=[O:32])[C:24]([OH:31])=[C:25]([C:27]([O:29][CH3:30])=[O:28])[N:26]=[C:10]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 673173728-tert-butyl 2-methyl 10-[benzyl(methyl)amino]-3-hydroxy-4-oxo-6,7,9,10-tetrahydropyrimido[1,2-d][1,4]diazepine-2,8(4H)-dicarboxylate

Product 1

HCID 57905695HCID 57905695, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

8-tert-butyl 2-methyl 10-[benzyl(methyl)amino]-3-hydroxy-4-oxo-6,7,9,10-tetrahydropyrimido[1,2-d][1,4]diazepine-2,8(4H)-dicarboxylate (prepared as described in Example 11, Step 1-4) was taken in CH2Cl2/TFA (8/2 v/v) and stirred at room temperature for 1 hour. Volatiles were evaporated and residue was triturated with diethyl ether. MS (ES) C18H22N4O4 requires 358. Found: 359 (M+H+). The crude organic product was dissolved in MeOH and treated with formaldehyde (3 eq.) and triethylamine (3 eq.). Acetic acid was added until pH=5.5, followed by NaCNBH3 (2 eq.), and resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated to a residue which was purified on Cation Exchange Resin (Varian Mega Bond Elute SCX). After washing with MeOH, the product was collected eluting with 2N NH3 solution in MeOH. The fractions containing the desired material were concentrated under reduced pressure to yield the title compound as a yellow oil. MS (ES) C19H24N4O4 requires 372. Found: 373 (M+H+).

Workup

  1. customVolatiles were evaporated
  2. customresidue was triturated with diethyl ether
  3. dissolutionThe crude organic product was dissolved in MeOH
  4. customresulting mixture
  5. stirringwas stirred overnight at room temperature
  6. concentrationThe reaction mixture was concentrated to a residue which
  7. customwas purified on Cation Exchange Resin (Varian Mega Bond Elute SCX)
  8. washAfter washing with MeOH
  9. customthe product was collected
  10. washeluting with 2N NH3 solution in MeOH
  11. additionThe fractions containing the desired material
  12. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-db731d94e06242869d84433607fb3e55
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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