Methanol → HCID 57685410, compound

HRID 1692752Notes

Reaction equation

HRID 1692752 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH:11]=O)=[N:8][C:6]=2[N:7]=1.[NH2:19][CH3:20].CO.[BH4-].[Na+]>C1(C)C=CC=CC=1.C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH2:11][NH:19][CH3:20])=[N:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 576853925-Chloro-7-morpholinothiazolo[4,5-d]pyrimidine-2-carbaldehyde

Product 1

HCID 57685410HCID 57685410, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 5-chloro-7-morpholinothiazolo[4,5-d]pyrimidine-2-carbaldehyde 43 in 50 mL Toluene and 50 mL THF was added 30 mL of NH2Me (40% in water) and the mixture stirred under N2 for two days. The mixture was concentrated in vacuo and redissolved in 50 mL THF and 50 mL MeOH followed by the portionwise addition of 1.6 g (4.0 eq) NaBH4 and the reaction mixture stirred overnight at room temperature. Complete reaction was confirmed by LCMS and the mixture was concentrated in vacuo and purified by flash chromatography (95/5% EtOAc/EtOH 20 min followed by a gradient up to 100% EtOH over 30 min more) to give 1-(5-chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)-N-methylmethanamine 60.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionredissolved in 50 mL THF
  3. stirringthe reaction mixture stirred overnight at room temperature
  4. customComplete reaction
  5. concentrationthe mixture was concentrated in vacuo
  6. custompurified by flash chromatography (95/5% EtOAc/EtOH 20 min
  7. waitfollowed by a gradient up to 100% EtOH over 30 min

Sources & evidence

ORD record
ord-f538007f50fe41c688f2c3904cd1a2e6
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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