2,6-Dichlorobenzaldehyde → 3-(2,6-Dichloro-benzylamino)-9-(2-hydroxy-4-methyl-pentyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

HRID 1826530Notes

Reaction equation

HRID 1826530 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH:14]([OH:19])[CH2:15][CH:16]([CH3:18])[CH3:17])[C:5]2=[N:4][C:3]=1[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1.[Cl:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:28]=1[CH:29]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.C(Cl)Cl>[Cl:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:28]=1[CH2:29][NH:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH:14]([OH:19])[CH2:15][CH:16]([CH3:18])[CH3:17])[C:5]2=[N:4][C:3]=1[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydride2×HCID 221395833-Amino-9-(2-hydroxy-4-methyl-pentyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

Product 1

HCID 221396273-(2,6-Dichloro-benzylamino)-9-(2-hydroxy-4-methyl-pentyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-9-(2-hydroxy-4-methyl-pentyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (100 mg, 0.29 mmol) and 2,6-dichlorobenzaldehyde (130 mg, 0.74 mmol) in 1 mL each of HOAc and CH2Cl2 was added NaBH(OAc)3 (110 mg, 0.52 mmol). The mixture was stirred at 40° C. for 50 min before a second portion of NaBH(OAc)3 (110 mg) was added. After a total of 2 h, the mixture was quenched with NaHCO3 (5 g) in H2O (15 mL) slowly and was allowed to stir over night at room temperature. Partition between CH2Cl2 and H2O followed by extraction with CH2Cl2 afforded the organic residue that was purified on silica (0–5% MeOH in DCM) to yield the desired product as an yellow foam. M+1 503.

Workup

  1. additionwas added
  2. customAfter a total of 2 h, the mixture was quenched with NaHCO3 (5 g) in H2O (15 mL) slowly
  3. customPartition between CH2Cl2 and H2O
  4. extractionfollowed by extraction with CH2Cl2
  5. customafforded the organic residue that
  6. customwas purified on silica (0–5% MeOH in DCM)

Sources & evidence

ORD record
ord-48aa4b8d31d544fa859c70ac39310786
Source dataset
uspto-grants-2006_05
Patent number
US07049318B2

Reaction notes

Loading…