Formic Acid → N-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-N-(1-methyl-pyrrolidin-3-yl)-methanesulfonamide

HRID 2098705Notes

Reaction equation

HRID 2098705 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([CH2:11][N:12]([CH:17]3[CH2:21][CH2:20][NH:19][CH2:18]3)[S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:6]=2[N:7]=1.[CH:28](O)=O.C=O>[OH-].[Na+]>[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([CH2:11][N:12]([CH:17]3[CH2:21][CH2:20][N:19]([CH3:28])[CH2:18]3)[S:13]([CH3:16])(=[O:14])=[O:15])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 86618409HCID 86618409, compound

Product 1

HCID 86618408N-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-N-(1-methyl-pyrrolidin-3-yl)-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-N-pyrrolidin-3-yl-methanesulfonamide (200 mg), formic acid (2.5 mL) and formaldehyde (37% solution, 0.37 mL) was heated at 60° C. overnight. The mixture was diluted with 2M NaOH then extracted with CH2Cl2. Combined extracts were dried (MgSO4), filtered and concentrated. Purification on silica yielded N-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-N-(1-methyl-pyrrolidin-3-yl)-methanesulfonamide (38 mg).

Workup

  1. extractionthen extracted with CH2Cl2
  2. dry with materialCombined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification on silica

Sources & evidence

ORD record
ord-3942a5ca57e344d8a01389737f00060b
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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